Methanol → 2-Amino-N-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonan-6-yl)-1-oxopropan-2-yl)-2-methylpropanamide

HRID 1036680Notes

Reaction equation

HRID 1036680 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:30][C:31](=[O:43])[C:32]([NH:35]C(=O)OC(C)(C)C)([CH3:34])[CH3:33])[C:11]([N:13]1[CH2:29][CH2:28][CH2:27][C:15]2([C:18](=[O:19])[N:17]([CH3:20])[CH:16]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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.CO>C(Cl)Cl>[NH2:35][C:32]([CH3:34])([CH3:33])[C:31]([NH:30][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]([N:13]1[CH2:29][CH2:28][CH2:27][C:15]2([C:18](=[O:19])[N:17]([CH3:20])[CH:16]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14]1)=[O:12])=[O:43]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 71060399tert-butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonan-6-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate

Product 1

HCID 710602252-Amino-N-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonan-6-yl)-1-oxopropan-2-yl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising tert-butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonan-6-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (290.8 mg, 0.491 mmol) and TFA (0.378 ml, 4.91 mmol) in DCM (3 ml) was stirred at room temperature for 90 minutes. The solvent was removed in vacuo to afford a colourless oil. The oil was dissolved with methanol (3 ml) and passed through a 10 g SCX2 cartridge eluting with 2M NH3 in methanol (70 ml). The solvent was removed in vacuo to yield the title compound as diastereomeric mixture.

Workup

  1. customThe solvent was removed in vacuo
  2. customto afford a colourless oil
  3. washeluting with 2M NH3 in methanol (70 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-236910cb946041a1b68e676359fff258
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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