Trifluoroacetic acid → HCID 86727331, compound

HRID 518981Notes

Reaction equation

HRID 518981 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[CH:27]([CH3:29])[CH3:28])[O:23][CH2:22][C:21]2[N:16]3[C@H:17]([CH3:31])[C:18](=[O:30])[NH:19][N:20]=2)[CH2:9]1)=O)(C)(C)C.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[NH:8]1[CH2:9][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[CH:27]([CH3:28])[CH3:29])[O:23][CH2:22][C:21]2[N:16]3[C@H:17]([CH3:31])[C:18](=[O:30])[NH:19][N:20]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727332HCID 86727332, compound

Product 1

HCID 86727331HCID 86727331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(7-isopropyl-4(R)-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (Enantiomer 1, SFC (Table 1, Method 11) Rt=2.948 min.; 0.33 g, 0.77 mmol) in DCM (8 mL) and TFA (2 mL) was stirred at ambient temperature for 2 h. The solvent was removed in vacuo to give 6-(azetidin-3-ylamino)-7-isopropyl-4(R)-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid as a pale yellow solid (Example #57-1, Enantiomer 1, SFC (Table 1, Method 11) Rt=3.79 min, 0.31 g, 92%). LC/MS (Table 1, Method 5) Rt=1.676 min.; MS m/z: 330 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ce1370f059ae464fbb9da9d0f0e4faa4
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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