(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester → 2-(S)-tert-butoxycarbonylamino-3-thiazol-2-yl-propionic acid benzyl ester

HRID 1039033Notes

Reaction equation

HRID 1039033 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:12](=[S:14])[NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](OC(OCC)([O-])CBr)[CH3:25]>C(COC)OC>[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:11][C:12]1[S:14][CH:24]=[CH:25][N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86654757(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl esterHCID 131730891Bromoacetate diethylacetal

Product 1

HCID 672357662-(S)-tert-butoxycarbonylamino-3-thiazol-2-yl-propionic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A 250 mL round bottom flask was charged with 2-(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester (1.0 g, 2.96 mmol), dimethoxyethane (66 mL), and bromoacetate diethylacetal (2.4 mL, 15.5 mmol). The flask containing the resulting mixture was fit with a reflux condenser and the mixture refluxed for 3 h. The resulting mixture was then concentrated in vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF65-400 g column, gradient 100:0-90:10 CH2Cl2:MeOH) to yield 2-(S)-tert-butoxycarbonylamino-3-thiazol-2-yl-propionic acid benzyl ester. 1H NMR (300 MHz, CDCl3) δ 7.67 (d, J=3.3 Hz, 1H), 7.29-7.44 (m, 5H), 7.20 (d, J=3.3 Hz, 1H), 5.15 (s, 2H), 5.75 (t, J=5.5 Hz, 1H), 73.15 (d, J=7.4 Hz, 1H), and 1.44 (s, 9H); MS (ES+) 363 (M+1).

Workup

  1. additionThe flask containing the resulting mixture
  2. customwas fit with a reflux condenser
  3. temperaturethe mixture refluxed for 3 h
  4. concentrationThe resulting mixture was then concentrated in vacuo
  5. customthe residue purified via flash silica gel chromatography (Analogix IF-280

Sources & evidence

ORD record
ord-0808ef5689a24b4787cdfd4f653e78b4
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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