Trifluoroacetic acid → HCID 71060274, compound

HRID 1036678Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C@@H:10]([NH:32][C:33](=[O:45])[C:34]([NH:37]C(=O)OC(C)(C)C)([CH3:36])[CH3:35])[C:11]([N:13]1[CH2:31][CH2:30][CH2:29][C:15]2([C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH:16]2[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=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.[OH-].[Na+]>C(Cl)Cl>[NH2:37][C:34]([CH3:36])([CH3:35])[C:33]([NH:32][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[CH2:31][CH2:30][CH2:29][C:15]2([C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH:16]2[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH2:14]1)=[O:12])=[O:45]

Participants

Conditions

Temperature: 7.5 °C

Procedure

To a stirred solution of tert-butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-p-tolyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (302 mg, 0.486 mmol) in DCM (3 ml) was added TFA (562 I, 7.30 mmol) at 5° C. The reaction mixture was then left to stir at 5-10° C. overnight. The reaction mixture was added to 2M NaOH (2 ml) and extracted with DCM (3×5 ml). The extracts were washed with brine (5 ml), dried (MgSO4) and concentrated to give the mixture of diastereomers. The desired isomer was isolated via SFC chromatography.

Workup

waitThe reaction mixture was then left
extractionextracted with DCM (3×5 ml)
washThe extracts were washed with brine (5 ml)
dry with materialdried (MgSO4)
concentrationconcentrated
customto give
additionthe mixture of diastereomers
customThe desired isomer was isolated via SFC chromatography

Sources & evidence

ORD record: ord-a78a6b9c036c450081838de070be0250
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546416B2

Reaction notes

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