Benzyl chloroformate → benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl](3-methylbutyl)carbamate

HRID 1524347Notes

Reaction equation

HRID 1524347 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24][OH:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>C(Cl)(Cl)Cl>[CH2:41]([O:40][C:38](=[O:39])[N:26]([C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86708047(5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-5-[(3-methylbutyl)amino]hexan-1-ol

Product 1

HCID 86708050benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl](3-methylbutyl)carbamateYield 67.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of the material from Step 5 (8 g, 18.11 mmol) in a 2:1 mixture of chloroform and saturated aqueous NaHCO3 (271 mL) was added benzyl chloroformate (2.59 mL, 118.11 mmol). The reaction mixture was stirred at room temperature for 1 hour, partitioned and extracted with chloroform. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes (10 to 70%) to yield 7 g of the title compound. LCMS (M+1)=576

Workup

  1. custompartitioned
  2. extractionextracted with chloroform
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2a5b393dc4c34cb6887016cd2e555922
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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