Methanol → HCID 71060100, compound

HRID 1036677Notes

Reaction equation

HRID 1036677 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:34][C:35](=[O:47])[C:36]([NH:39]C(=O)OC(C)(C)C)([CH3:38])[CH3:37])[C:11]([N:13]1[CH2:33][CH2:32][CH2:31][C:15]2([C:19](=[O:20])[N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH:16]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=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>[NH2:39][C:36]([CH3:38])([CH3:37])[C:35]([NH:34][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[CH2:33][CH2:32][CH2:31][C:15]2([C:19](=[O:20])[N:18]([CH:21]([CH3:22])[CH3:23])[CH2:17][CH:16]2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:14]1)=[O:12])=[O:47]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 71060476HCID 71060476, compound

Product 1

HCID 71060100HCID 71060100, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising tert-butyl 1-((2R)-3-(benzyloxy)-1-(4-(4-fluorophenyl)-2-isopropyl-1-oxo-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (378 mg, 0.579 mmol) (step 1) and TFA (0.892 ml, 11.58 mmol) in DCM (4 ml) was stirred at room temperature for 4 hours. 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 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 colourless oil
  3. washeluting with 2M NH3 in methanol (70 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-10ca30eee4904f2eb86f051b70437c2a
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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