Trifluoroacetic acid → HCID 86727486, compound

HRID 519108Notes

Reaction equation

HRID 519108 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[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:36])[C:18](=[O:35])[NH:19][N:20]=2)[CH2:9]1)=O)(C)(C)C.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[NH:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:36])[C:18](=[O:35])[NH:19][N:20]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727484HCID 86727484, compound

Product 1

HCID 86727486HCID 86727486, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(7-benzyloxy-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.028 g, 0.057 mmol) in TFA (0.5 mL) and DCM (3 mL) was stirred at rt for 2 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (Table 3, Method 18) to give 6-(azetidin-3-ylamino)-7-benzyloxy-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (0.013 g, 58%). LC/MS (Table 1, Method 5) Rt=2.201 min; MS m/z: 394 [M+H]+

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC (Table 3, Method 18)

Sources & evidence

ORD record
ord-db6ad1401f6a48d097a593bfa285d514
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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