Trifluoroacetic acid → HCID 59547308, compound

HRID 2038579Notes

Reaction equation

HRID 2038579 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@:8]2([CH2:13][C:12](=[O:14])[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH2:10]2)[CH2:7][N:6]1[C:22](=[O:36])[C@@H:23]([NH:28]C(OC(C)(C)C)=O)[C:24]([CH3:27])([CH3:26])[CH3:25])=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:28][C@@H:23]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]([N:6]1[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:9][C@@:8]2([CH2:13][C:12](=[O:14])[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH2:10]2)[CH2:7]1)=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59547289HCID 59547289, compound

Product 1

HCID 59547308HCID 59547308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (3S,5R)-methyl-2-((S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)-7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (C7a) (36.9 mg, 70.6 pimp was dissolved in CH2Cl2 (1.0 ml) and treated with trifluoroacetic acid (0.3 ml) for 6 hrs at room temperature. The reaction was concentrated to dryness to give (3S,5R)-methyl 2-((S)-2-amino-3,3-dimethylbutanoyl)-7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (D7a) (70.6 μmol). The minor diastereomer (3S,5S)-methyl-2-((S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)-7-(3-chloro phenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (C7b) (9.4 mg, 18 μmol) was treated similarly to give (3S,5S)-methyl 2-((S)-2-amino-3,3-dimethylbutanoyl)-7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (D7b) (18 μmol, 100%).

Workup

  1. concentrationThe reaction was concentrated to dryness

Sources & evidence

ORD record
ord-eceba249a0f54a6288685c9b079e2f84
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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