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

HRID 366908
Notes
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Reaction equation

HRID 366908 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 10808734(R)-Benzyl (4-chloro-3-oxo-1-(phenylthio)butan-2-yl)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776Isopropanol
Solvent

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 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-da1f0146ade84064a14ab3983f3b8ee3
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06130348

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes