Bromoacetic Acid → 2-Benzyloxycarbonylamino-3-(bromoactyl-prop-2-ynyl-amino)-propionic acid methyl ester

HRID 1432922Notes

Reaction equation

HRID 1432922 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[Br:16][CH2:17][C:18](O)=[O:19].[CH3:21][O:22][C:23](=[O:41])[CH:24]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:25][NH:26][CH2:27][C:28]#[CH:29]>C(Cl)Cl.CCOCC>[CH3:21][O:22][C:23](=[O:41])[CH:24]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH2:25][N:26]([C:18](=[O:19])[CH2:17][Br:16])[CH2:27][C:28]#[CH:29]

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 544236402-Benzyloxycarbonylamino-3-(prop-2-ynylamino)-propionic acid methyl ester

Product 1

HCID 1317277242-Benzyloxycarbonylamino-3-(bromoactyl-prop-2-ynyl-amino)-propionic acid methyl esterYield 47.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

DCC (2.27 g, 11.0 mmol) and bromoacetic acid (1.48 g, 10.7 mmol) is added to a solution of 2-benzyloxycarbonylamino-3-(prop-2-ynylamino)-propionic acid methyl ester (3.10 g, 10.7 mmol) in CH2Cl2 at RT. The mixture is stirred overnight then diluted with ether. The white solid which precipitates out is filtered and the filtrate is concentrated to give a yellow oil. The crude product is purified by chromatography eluting with a gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes to yield the title product (2.1 g, 5.12 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ7.30 (m, 5H), 5.70 (d, 1H), 5.10 (s, 2H), 4.63 (m, 1H), 4.15 (d, 2H), 4.00 (m, 1H), 3.80 (s, 3H), 3.75 (s, 2H), 3.70 (dd, 1H), 2.27 (bs, 1H). Ion spray MS, [M+H]+=411, 413, Br pattern.

Workup

  1. customThe white solid which precipitates out
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated
  4. customto give a yellow oil
  5. customThe crude product is purified by chromatography
  6. washeluting with a gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-356294f83e544092bde454bc39068ad5
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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