Hydrochloric Acid → Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

HRID 259913Notes

Reaction equation

HRID 259913 reaction equation
[CH2:1]([C@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C:9](=[O:12])[CH2:10][Cl:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C(O)C>[CH2:1]([C@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C@H:9]([OH:12])[CH2:10][Cl:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 9881533methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate

Product 1

HCID 10945089Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamateYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33.06 g of lithium aluminum tri-tert.-butoxyhydride were added portionwise at -15° C. to a suspension of 25.57 g of methyl (S)(1-benzyl-3-chloro-2-oxo-propyl)-carbamate in 280 ml of ethanol and the mixture was subsequently hydrolyzed at 0° C. with 140 ml of 3N hydrochloric acid and 170 ml of water. The suspension was concentrated to 370 ml, filtered and the residue was washed with water/ethanol (4:1) and dried, yielding 23.27 g (90%) of isomerically-pure methyl (1S,2S)-(1-benzyl-3-chloro-2-hydroxy- propyl)-carbamate, m.p. 163°-164.5° C. IR (KBr): 3323s, br. (NH, OH), 1689 (C=O), 1546s (amide II).

Workup

  1. concentrationThe suspension was concentrated to 370 ml
  2. filtrationfiltered
  3. washthe residue was washed with water/ethanol (4:1)
  4. customdried

Sources & evidence

ORD record
ord-1902f2a971684ed7a2eef711806fa486
Source dataset
uspto-grants-1996_06
Patent number
US05523463

Reaction notes

Loading…