Hydrochloric Acid → Benzyl [(2R,3S)-4-chloro-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate

HRID 1979094Notes

Reaction equation

HRID 1979094 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[Cl:14][CH2:15][C:16](=[O:37])[C@@H:17]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C(O)(C)C>[Cl:14][CH2:15][C@@H:16]([OH:37])[C@@H:17]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 10808734Z-D-Phe chloromethyl ketone

Product 1

HCID 9951031Benzyl [(2R,3S)-4-chloro-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2.15 g aluminium isopropoxide in 35 ml of isopropanol were added 3.64 g of benzyl [3-chloro-2-oxo-(R)-1-(phenylthiomethyl)-propyl]-carbamate and the mixture was stirred at 50° C./400 mbar for 4 hours. The mixture was cooled to 0° C., the pH was adjusted to 1 by adding hydrochloric acid and the isopropanol was evaporated. The residue was partitioned between water and dichioromethane and the organic layer was evaporated. The residue was chromatographed on silica to give 2.9 g (80%) of pure benzyl (1R, 2S)-[3-chloro-2-hydroxy-1-(phenylthiomethyl)-propyl]-carbamate. IR (KBr): 3360br (NH, OH), 1690s (C═O), 1540s (amide II).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe isopropanol was evaporated
  3. customThe residue was partitioned between water and dichioromethane
  4. customthe organic layer was evaporated
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-e6427cefed5842018710588906aa1fe3
Source dataset
uspto-grants-2001_05
Patent number
US06239296B1

Reaction notes

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