Methanol → HCID 71060189, compound

HRID 1036674Notes

Reaction equation

HRID 1036674 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]3([CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:45])[C@H:19]([NH:31][C:32](=[O:44])[C:33]([NH:36]C(=O)OC(C)(C)C)([CH3:35])[CH3:34])[CH2:20][C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]([CH3:30])[CH:22]=4)[CH2:13]3)[C:11](=[O:46])[N:10]([CH:47]([CH3:49])[CH3:48])[CH2:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[NH2:36][C:33]([CH3:35])([CH3:34])[C:32]([NH:31][C@H:19]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]([CH3:30])[CH:22]=1)[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C:12]2([C:11](=[O:46])[N:10]([CH:47]([CH3:48])[CH3:49])[CH2:9][CH:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:13]1)=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 71060508HCID 71060508, compound

Product 1

HCID 71060189HCID 71060189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising tert-butyl 1-((2R)-1-(4-(4-fluorophenyl)-2-isopropyl-1-oxo-2,7-diazaspiro[4.5]decan-7-yl)-3-(1-methyl-1H-indol-3-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (378 mg, 0.559 mmol) (step 1) and TFA (0.431 ml, 5.59 mmol) in DCM (3 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-dc7c96f0a057406dbae485b503f7cded
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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