Triethylamine → methyl 2-((R)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxypropanoate

HRID 2070994Notes

Reaction equation

HRID 2070994 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].CCN(CC)CC.[C:17]([NH:24][C@@H:25]([C:27](O)=[O:28])[CH3:26])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:20]([O:19][C:17]([NH:24][C@H:25]([CH3:26])[C:27]([NH:6][CH:5]([CH2:7][OH:8])[C:4]([O:3][CH3:2])=[O:9])=[O:28])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 637606BOC-D-alanineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 57486672methyl 2-((R)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxypropanoateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of L-Serine methyl ester hydrochloride (5.0 g, 32.0 mmol), in CH2Cl2 (150 mL) at 0° C., were added Et3N (4.88 mL, 35.2 mmol), Boc-D-Alanine (6.06 g, 32 mmol), and DCC (7.26 g, 35.2 mmol) sequentially. The reaction was allowed to warm to room temperature and stirred overnight. All the solvent was evaporated and the residue was triturated with ethyl acetate and the precipitate was filtered off. The filtrate was concentrated under low pressure and chromatographed on silica gel (70% ethyl acetate/30% chloroform) to yield 86% of methyl 2-((R)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxypropanoate.

Workup

  1. customAll the solvent was evaporated
  2. customthe residue was triturated with ethyl acetate
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated under low pressure
  5. customchromatographed on silica gel (70% ethyl acetate/30% chloroform)

Sources & evidence

ORD record
ord-e0f10590b7fc40e4bc6962dcbbe04f50
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…