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

HRID 2304789Notes

Reaction equation

HRID 2304789 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./400mbar 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 dichloromethane 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): 3360 br (NH, OH), 1690 s (C═O), 1540 s (amide II).

Workup

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

Sources & evidence

ORD record
ord-106029996b244de398fb9a9adfe762ed
Source dataset
uspto-grants-2002_08
Patent number
US06437134B1

Reaction notes

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