(R)-5-(4-Benzyloxy-phenyl)-4-tert-butoxycarbonylamino-pent-2-enoic acid methyl ester → 4-Amino-5-(4-benzyloxy-phenyl)-pent-2-enoic acid methyl ester

HRID 852867Notes

Reaction equation

HRID 852867 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]=[CH:5][C@H:6]([NH:22]C(OC(C)(C)C)=O)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3](=[O:30])[CH:4]=[CH:5][CH:6]([NH2:22])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 69415648(R)-5-(4-Benzyloxy-phenyl)-4-tert-butoxycarbonylamino-pent-2-enoic acid methyl ester

Product 1

HCID 694191804-Amino-5-(4-benzyloxy-phenyl)-pent-2-enoic acid methyl esterYield 98.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-5-(4-Benzyloxy-phenyl)-4-tert-butoxycarbonylamino-pent-2-enoic acid methyl ester (3.0 g, 0.0073 mol) was added to TFA (10 ml) at 0° C. with stirring. After 10 min, ice was added, and the mixture extracted into EtOAc. The extracts were washed with K2CO3 solution (20% w/v) and brine, dried with MgSO4, and evaporated to afford 2.23 g (98%) of the title compound.

Workup

  1. additionice was added
  2. extractionthe mixture extracted into EtOAc
  3. washThe extracts were washed with K2CO3 solution (20% w/v) and brine
  4. dry with materialdried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-2f0a5f14bc304251b97f7ebb01f7fd73
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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