Triethylamine → methyl (2R)-2-[(t-butoxycarbonyl)amino]-4-oxo-4-[4-(9H-thioxanthen-9-ylidene)-1-piperidinyl]butanoate

HRID 2061256Notes

Reaction equation

HRID 2061256 reaction equation
Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH:20]1[C:33]2[C:32](=[C:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[S:25][C:24]=2[CH:23]=[CH:22][CH:21]=1.[C:40]([O:44][C:45]([NH:47][C@H:48]([C:53]([O:55][CH3:56])=[O:54])[CH2:49][C:50](O)=[O:51])=[O:46])([CH3:43])([CH3:42])[CH3:41].[Cl-].[NH4+]>ClCCl>[C:40]([O:44][C:45]([NH:47][C@H:48]([CH2:49][C:50](=[O:51])[N:37]1[CH2:38][CH2:39][C:34](=[C:32]2[C:33]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[S:25][C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:35][CH2:36]1)[C:53]([O:55][CH3:56])=[O:54])=[O:46])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11021202(3S)-3-(((tert-butoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acidHCID 130525974-(9H-thioxanthen-9-ylidene)piperidine

Product 1

HCID 86594136methyl (2R)-2-[(t-butoxycarbonyl)amino]-4-oxo-4-[4-(9H-thioxanthen-9-ylidene)-1-piperidinyl]butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g (5.22 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 0.73 ml (5.24 mmol) of triethylamine and 1.351 g (4.84 mmol) of 4-(9H-thioxanthen-9-ylidene)piperidine were added to 1.290 g (5.22 mmol) of (S)-3-[(t-butoxycarbonyl)amino]-4-methoxy-4-oxobutanoic acid in 20 ml of dichloromethane in an ice bath, and they were stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1) to obtain the title compound.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1)

Sources & evidence

ORD record
ord-1d402f62ae8f4e73b7346f78b3cc10a6
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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