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

HRID 1979094
Notes
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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
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 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06239296B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes