Trifluoroacetic acid → HCID 68422702, compound

HRID 881818Notes

Reaction equation

HRID 881818 reaction equation
Cl.[NH2:2][C@H:3]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:13][CH:12]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].COC1C=CC(C[N:31]2[N:35]=[N:34][C:33]([C:36](Cl)=[O:37])=[N:32]2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][C@H:3]([NH:2][C:36]([C:33]1[N:32]=[N:31][NH:35][N:34]=1)=[O:37])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:13][CH:12]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 596077322-(4-Methoxy-benzyl)-2H-tetrazole-5-carbonyl chlorideHCID 86648190(R)-ethyl 3-amino-4-(3'-chlorobiphenyl-4-yl)butanoate hydrochloride

Product 1

HCID 68422702HCID 68422702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate 8-1 in DCM (8 ml) at room temperature is added 2-(4-methoxy-benzyl)-2H-tetrazole-5-carbonyl chloride and followed by TEA (Intermediate 22: 0.293 ml, 2.100 mmol). The reaction is stirred at room temperature for 5 min. The reaction is quenched by brine and is extracted with DCM. The combined organic layer is washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by column chromatography (15% to 40% EtOAc/Heptane). The obtained residue in TFA (5 ml, 64.9 mmol) is heated at 80° C. for 0.5 hours. The reaction is concentrated under reduced pressure to give (R)-4-(3′-chloro-biphenyl-4-yl)-3-[(2H-tetrazole-5-carbonyl)-amino]-butyric acid ethyl ester.

Workup

  1. customThe reaction is quenched by brine
  2. extractionis extracted with DCM
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography (15% to 40% EtOAc/Heptane)
  8. concentrationThe reaction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-386bfd0e87bd42fbac3257ace83b0289
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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