Triethylamine → (R)-2-(5-Thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic Acid Methyl Ester

HRID 970796Notes

Reaction equation

[OH:1][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[CH:8][C:6]=2[CH:7]=1.[CH3:17][O:18][C:19](=[O:31])[C@H:20]([N:28]=[C:29]=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C1COCC1>[CH3:17][O:18][C:19](=[O:31])[C@H:20]([NH:28][C:29]([O:1][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[CH:8][C:6]=2[CH:7]=1)=[O:30])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-hydroxymethyl-5-thiophen-3-yl-benzofuran 22 (0.31 g, 1.35 mmole), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (0.33 g, 1.6 mmole), triethylamine (0.43 ml), and THF (25 ml) was heated to 50° C. under a nitrogen atmosphere for 14 hrs. The solvent was removed under reduced pressure and the residue was purified by chromatography giving about 0.28 g of (R)-2-(5-thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenylpropionic acid methyl ester 23, mp. 105-106° C.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by chromatography

Sources & evidence

ORD record: ord-b6a9f8dd59554d8294bf2cebea7e80e4
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312230B2

Reaction notes

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