Methanol → HCID 71060292, compound

HRID 1036672Notes

Reaction equation

HRID 1036672 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:44])[C@H:19]([NH:30][C:31](=[O:43])[C:32]([NH:35]C(=O)OC(C)(C)C)([CH3:34])[CH3:33])[CH2:20][C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][CH:22]=4)[CH2:13]3)[C:11](=[O:45])[N:10]([CH3:46])[CH2:9]2)=[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:19]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C:12]2([C:11](=[O:45])[N:10]([CH3:46])[CH2:9][CH:8]2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:13]1)=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acid2×HCID 71060347HCID 71060347, compound

Product 1

HCID 71060292HCID 71060292, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising tert-butyl 1-((2R)-1-(4-(4-fluorophenyl)-2-methyl-1-oxo-2,7-diazaspiro[4.5]decan-7-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (312.3 mg, 0.493 mmol) (step 1) and TFA (0.380 ml, 4.93 mmol) in DCM (3 ml) was stirred at room temperature for 17 hours. TFA (1 mL, 13 mmol) was added to the reaction mixture. After 3 h 45 min 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. customAfter 3 h 45 min the 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-70063d6337b34892a0de36fd147f7640
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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