HCID 178454208, compound → HCID 178511821, compound

HRID 491879Notes

Reaction equation

HRID 491879 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([CH2:37][CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:18](=[O:36])[CH2:19][CH2:20][C@H:21]([NH:28]C(OC(C)(C)C)=O)[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([C:18](=[O:36])[CH2:19][CH2:20][C@H:21]([NH2:28])[CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH2:37][CH2:38][O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178454208HCID 178454208, compound

Product 1

HCID 178511821HCID 178511821, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-{(2-benzyloxy-ethyl)-[4-tert-butoxycarbonylamino-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-amino}-cis-cyclohexanecarboxylic acid benzyl ester (4.8 g, 7.5 mmol) in TFA (5% in CH2Cl2, 100 mL) was stirred at room temperature overnight. The solvent and most of the TFA was evaporated, and EtOAc (300 mL) was added to the residue. The solution was washed with aq. NaHCO3 and aq. NaCl. The organic layer was dried with MgSO4 and evaporated to yield 4-[[4-amino-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cis-cyclohexanecarboxylic acid benzyl ester as a light brown oil.

Workup

  1. customThe solvent and most of the TFA was evaporated
  2. additionEtOAc (300 mL) was added to the residue
  3. washThe solution was washed with aq. NaHCO3 and aq. NaCl
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-eeb12315351c431192f1175cbc824ffb
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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