Sodium borohydride → HCID 14796009, compound

HRID 476802Notes

Reaction equation

HRID 476802 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9](=[O:15])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C.CCOCC>[CH:1]1([CH2:7][C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C@@H:9]([OH:15])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14796007HCID 14796007, compound

Product 1

HCID 14796009HCID 14796009, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The product from part (c) (2.73 g., 8.07 mmole) is dissolved in absolute ethanol (50 ml.) and cooled to 5°. Sodium borohydride (0.6 g., 16.14 mmole) is added portionwise and the reaction mixture is stirred for one hour, diluted with ether (200 ml.), and quenched with 1N HCl to pH 1. The organic layer is separated, washed twice with water and brine, dried (MgSO4), and concentrated in vacuo. The two isomers are separated by flash chromatography on silica gel (Merck, 300 g.) eluting with ethyl acetate:hexane (3:8). The slower moving isomer is identified as the S,S configuration and the faster moving isomer is identified as (1S,2R)-[1-(cyclohexylmethyl)-2-hydroxy-2-(2-thiazolyl)ethyl]carbamic acid, 1,1-dimethylethyl ester; [α]D =-30.72° (c=0.55, methanol). TLC (silica gel; ethyl acetate:hexane; 1:1) Rf =0.70.

Workup

  1. temperaturecooled to 5°
  2. customquenched with 1N HCl to pH 1
  3. customThe organic layer is separated
  4. washwashed twice with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe two isomers are separated by flash chromatography on silica gel (Merck, 300 g.)
  8. washeluting with ethyl acetate:hexane (3:8)
  9. custom[α]D =-30.72° (c=0.55, methanol)

Sources & evidence

ORD record
ord-8ba98706e31a4171987ddf3b34452922
Source dataset
uspto-grants-1989_12
Patent number
US04885292

Reaction notes

Loading…