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Triethylamine → HCID 14129895, compound

HRID 1731398
Notes
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Reaction equation

HRID 1731398 reaction equation
C(C[CH2:5][N:6]([CH3:24])[C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@H:10]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:8])(O)=O.C(Cl)(=O)C(Cl)=O.[C:31]1([C:37]2[O:38][C:39](=[O:52])[CH:40]([CH2:42][C:43]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[NH:45][CH:44]=3)[N:41]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>CN(C)C=O.O1CCCC1>[C:37]([NH:41][CH:40]([CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1)[C:39](=[O:52])[CH2:5][N:6]([CH3:24])[C:7]([N:9]1[CH2:23][CH2:22][CH2:21][C@H:10]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:8])(=[O:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13657320HCID 13657320, compoundHCID 136573274-[(1H-Indol-3-yl)methyl]-2-phenyl-1,3-oxazol-5(4H)-one

Product 1

HCID 14129895HCID 14129895, compound

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

1-[[[(2-Carboxyethyl)methylamino]carbonyl]-L-proline, phenylmethyl ester (3.2 g., 10 mmole) is taken into 33 ml. of dry tetrahydrofuran with stirring at 5°. Oxalyl chloride (1.05 ml., 12 mmole) is added dropwise followed by 4 drops of dimethylformamide. After 20 minutes the ice bath is removed and after stirring for one hour at room temperature the reaction mixture is concentrated to dryness, taken into 20 ml. of tetrahydrofuran, chilled and added dropwise to 2-phenyl-4-[(1H-indol-3-yl)methyl]-5(4H)-oxazolone (3.0 g., 10.5 mmole) in 16 ml. of dry tetrahydrofuran with stirring in an ice bath. Triethylamine (1.7 ml., 12 mmole) is then added to the reaction mixture. After 15 minutes the ice bath is removed and the reaction is run overnight at room temperature. The triethylamine hydrochloride salt is filtered off and the filtrate is concentrated to dryness, taken into 10.6 ml. of pyridine, 33.3 mg. of 4-dimethylamino pyridine is added, and the mixture is stirred for 3 hours. Acetic acid (10.6 ml.) is added and the reaction is heated for 45 minutes at 100° under an argon atmosphere. The reaction mixture is concentrated to dryness, taken into ethyl acetate, and washed with saturated sodium bicarbonate and dilute hydrochloric acid. The crude product (4.6 g.) is purified on a silica gel column in ethyl acetate: benzene (2:1) to yield 523 mg. of (±)-1-[[[3-(benzoylamino)-4-(1H-indol-3-yl)-2-oxbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester.

Workup

  1. customAfter 20 minutes the ice bath is removed
  2. concentrationis concentrated to dryness
  3. temperatureof tetrahydrofuran, chilled
  4. customAfter 15 minutes the ice bath is removed
  5. waitthe reaction is run overnight at room temperature
  6. filtrationThe triethylamine hydrochloride salt is filtered off
  7. concentrationthe filtrate is concentrated to dryness
  8. additionof 4-dimethylamino pyridine is added
  9. stirringthe mixture is stirred for 3 hours
  10. additionAcetic acid (10.6 ml.) is added
  11. temperaturethe reaction is heated for 45 minutes at 100° under an argon atmosphere
  12. concentrationThe reaction mixture is concentrated to dryness
  13. washwashed with saturated sodium bicarbonate and dilute hydrochloric acid
  14. customThe crude product (4.6 g.) is purified on a silica gel column in ethyl acetate: benzene (2:1)
  15. customto yield 523 mg

Sources & evidence

ORD record
ord-32b28f0e88504f468ea3313c3aed6c92
Source dataset
uspto-grants-1986_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04621092

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes