Methanol → N-((2R)-3-(1H-indol-3-yl)-1-(2-isopropyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-yl)-2-amino-2-methylpropanamide

HRID 1036682Notes

Reaction equation

HRID 1036682 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH:34][C:35](=[O:47])[C:36]([NH:39]C(=O)OC(C)(C)C)([CH3:38])[CH3:37])[C:12]([N:14]2[CH2:33][CH2:32][CH2:31][C:16]3([C:20](=[O:21])[N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH:17]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:15]2)=[O:13])=[CH:2]1.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH:34][C:35](=[O:47])[C:36]([NH2:39])([CH3:38])[CH3:37])[C:12]([N:14]2[CH2:33][CH2:32][CH2:31][C:16]3([C:20](=[O:21])[N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH:17]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:15]2)=[O:13])=[CH:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 71060502tert-butyl 1-((2R)-3-(1H-indol-3-yl)-1-(2-isopropyl-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 71060440N-((2R)-3-(1H-indol-3-yl)-1-(2-isopropyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-yl)-2-amino-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising tert-butyl 1-((2R)-3-(1H-indol-3-yl)-1-(2-isopropyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (450.21 mg, 0.699 mmol) (step 1) and TFA (0.539 ml, 6.99 mmol) in DCM (5 ml) was stirred at room temperature for 17 hours. The solvent was removed in vacuo to afford a purple oil. The oil was dissolved with methanol (3 ml) and passed through a 10 g SCX-2 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 purple oil
  3. washeluting with 2M NH3 in methanol (70 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e7b1ddf16b0f4d5c8bd3380358791184
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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