Benzyl chloroformate → Boc-dap(Z)-OH

HRID 1504818Notes

Reaction equation

HRID 1504818 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:12]([OH:14])=[O:13])[NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C1COCC1.O>[CH2:27]([O:26][C:24]([NH:1][CH2:2][C@@H:3]([C:12]([OH:14])=[O:13])[NH:4][C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2755946Boc-Dap-OH

Product 1

HCID 2755950Boc-dap(Z)-OH

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-amino-N-(tert-butoxycarbonyl)alanine (5.0 g, 25 mmol), potassium hydroxide (1.6 g, 29 mmol) and potassium carbonate (6.9 g, 29 mmol) in THF (60 mL) and water (20 mL) was added dropwise benzyl chloroformate (5.0 g, 29 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, the reaction mixture was concentrated under reduced pressure, and the residue was washed with water followed by petroleum ether to afford 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine. MS ESI calc'd. for C16H23N2O6 [M+H]+ 339. found 339. 1H NMR (300 MHz, CD3OD) δ 7.33-7.26 (m, 5H), 5.03 (s, 2H), 4.03-4.01 (m, 1H), 3.49-3.35 (m, 2H), 1.44 (s, 9H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with water

Sources & evidence

ORD record
ord-0e00d8a05e404b75a216457608dced05
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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