Methanol → HCID 71060189, compound

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

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.