2-Thiopheneacetic acid → HCID 9928730, compound

HRID 1058992Notes

Reaction equation

HRID 1058992 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([C:10]([O:12][CH3:13])=[O:11])[C@H:7]([CH2:14][N:15]=[N+]=[N-])[C@@H:6]1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:4].S1C=CC=C1[CH2:31][C:32](O)=[O:33]>>[C:22]([O:21][C:19]([NH:18][C@H:6]1[C@@H:7]([CH2:14][NH:15][C:32](=[O:33])[CH3:31])[C@H:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:9][C@@H:5]1[C:3]([OH:2])=[O:4])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 159702-Thiopheneacetic acidHCID 59039519HCID 59039519, compound

Product 1

HCID 9928730HCID 9928730, compoundYield 48%

Procedure

(±)-(1S,2S,3R,4R)-2-(t-Butyloxycarbonylamino)-3-(azidomethyl)-cyclopentane-1,4-dicarboxylic acid dimethyl ester (506 mg, 1.42 mmole) and thiolacetic acid (0.4 mL) were reacted at room temperature for 6 hours. The reaction mixture was concentrated in vacuo and the crude product was purified by silica gel chromatography using 3% methanol in chloroform to provide the title compound (yield: 255 mg, 48%). MS: (M+H)+=373.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-eddf7fd98ad0456ea318bfea6333ad32
Source dataset
uspto-grants-2003_02
Patent number
US06518305B1

Reaction notes

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