Trifluoroacetic acid → 2-Amino-N-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-yl)-2-methylpropanamide

HRID 1036670Notes

Reaction equation

HRID 1036670 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:31][C:32](=[O:44])[C:33]([NH:36]C(=O)OC(C)(C)C)([CH3:35])[CH3:34])[C:11]([N:13]1[CH2:30][CH2:29][CH2:28][C:15]2([C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH:16]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:36][C:33]([CH3:35])([CH3:34])[C:32]([NH:31][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:11]([N:13]1[CH2:30][CH2:29][CH2:28][C:15]2([C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH:16]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:14]1)=[O:12])=[O:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86674094tert-Butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate

Product 1

HCID 710601762-Amino-N-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-yl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (1.18 g, 1.945 mmol) in DCM (15 ml) was treated with TFA (7 ml, 91 mmol) and stirred at RT for 1 hour. The solvent was removed in vacuo and the residue was partitioned between EtOAc (200 ml) and sat. sodium bicarbonate solution (100 ml). The organic portion was dried (MgSO4) and concentrated in vacuo to afford the title compound as a diastereomeric mixture;

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc (200 ml) and sat. sodium bicarbonate solution (100 ml)
  3. dry with materialThe organic portion was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af89bc5bc2a04679be990221803ba1c1
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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