Propargyl bromide → 2-Benzyloxycarbonylamino-3-(prop-2-ynylamino)-propionic acid methyl ester

HRID 1432921Notes

Reaction equation

[CH2:1](Br)[C:2]#[CH:3].Cl.[CH3:6][O:7][C:8](=[O:23])[CH:9]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:10][NH2:11].C(N(CC)CC)C>C1COCC1>[CH3:6][O:7][C:8](=[O:23])[CH:9]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:10][NH:11][CH2:3][C:2]#[CH:1]

Participants

Conditions

Temperature: 50 °C

Procedure

Propargyl bromide (1.6 mL, 14.4 mmol) is added to a solution of 3-amino-2-benzyloxycarbonylamino-propionic acid methyl ester hydrochloride (4.0 g, 13.9 mmol) and triethylamine (4.1 mL, 29.4 mmol) in THF (46 mL). The resulting mixture is heated to 50° C. and stirred overnight then cooled to RT and concentrated in vacuo. The crude residue is diluted with methylene chloride, washed with saturated NaHCO3 and brine then the organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude material (4.0 g) is taken on to the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ7.25-7.30 (m, 5H), 5.75 (bs, 1H), 5.20 (s, 2H), 4.45 (bs, 1H), 3.80 (s, 3H), 3.75 (m, 1H), 3.31 (s, 2H), 3.08 (dd, 1H), 2.98 (dd, 1H), 2.20 (t, 1H). EI MS, [M+H]+=291.

Workup

temperaturethen cooled to RT
concentrationconcentrated in vacuo
additionThe crude residue is diluted with methylene chloride
washwashed with saturated NaHCO3 and brine
dry with materialthe organic layer is dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material (4.0 g) is taken on to the subsequent step without further purification

Sources & evidence

ORD record: ord-03b821690b30428bb9fe4c28ee0ed4d3
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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