Benzyl chloroformate → HCID 148550093, compound

HRID 1438185Notes

Reaction equation

HRID 1438185 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([O:26][CH2:27][CH3:28])[CH:17]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].C(=O)(O)[O-].[Na+].Cl[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>ClCCl>[CH2:38]([O:37][C:35]([NH:3][C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([O:26][CH2:27][CH3:28])[CH:17]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1)=[NH:2])=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 57942791HCID 57942791, compound

Product 1

HCID 148550093HCID 148550093, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 141D (6.7 g; 13.25 mmol) in dichloromethane (80 mL) was added sodium bicarbonate (132 mL, 1 M). Benzyl chloroformate (1.89 mL, 13.25 mmol) in dichloromethane (20 mL) was then added dropwise using an addition funnel over a period of 1 h. After the addition was complete, the suspension turned to a clear orange solution. The layers were separated and the organic layer was washed with brine and dried over sodium sulfate. The solvent was removed and the crude residue was purified by flash column chromatography to give 4.6 g of 141E as a yellow solid (69% yield). LC-MS: 520.10 (M+H)+.

Workup

  1. customof 1 h
  2. additionAfter the addition
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed
  7. customthe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ab6fa8f5e92c4c55ab0bbb98e0889606
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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