Triethylamine → HCID 18392430, compound

HRID 619841Notes

Reaction equation

HRID 619841 reaction equation
[C:1]([C:3]1[S:7][CH:6]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([N:14]([S:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=4)[CH:23]=3)(=[O:21])=[O:20])[CH2:15][C:16](O)=[O:17])[C:10]2=[O:34])[CH:4]=1)#[N:2].C([N:37](CC)CC)C.ClC(OCC)=O.[NH4+].[OH-]>C1COCC1.CCOC(C)=O>[C:1]([C:3]1[S:7][CH:6]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([N:14]([S:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=4)[CH:23]=3)(=[O:21])=[O:20])[CH2:15][C:16]([NH2:37])=[O:17])[C:10]2=[O:34])[CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 18392431HCID 18392431, compound

Product 1

HCID 18392430HCID 18392430, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[[1-(5-cyanothiophene-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-(7-methoxynaphthalene-2-sulfonyl)amino]acetic acid (0.40 g, 0.80 mmol) in 6 mL of THF at -15° C. is added triethyl amine (0.10 g, 0.96 mmol) and ethyl chloroformate (0.09 g, 0.84 mmol). The solution is stirred for 1 hour. After this time, NH4OH (0.07 mL, 0.90 mmol) is added and the solution is allowed to warm to ambient temperatures. After 16 hours, the solution is diluted with EtOAc. The solution is washed with 1 N HCl, sat. NaHCO3 and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The title compound (0.28 g, 0.56 mmol) is obtained as a white foam.

Workup

  1. temperatureto warm to ambient temperatures
  2. waitAfter 16 hours
  3. washThe solution is washed with 1 N HCl, sat. NaHCO3 and sat. NaCl
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bfaf4eeb73cd4affbd1d77ffc7d88a57
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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