Trifluoroacetic acid → HCID 178512540, compound
Reaction equation
[NH:1]([C:5]1[CH:52]=[CH:51][C:8]([C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([N:22]3[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]3)=[O:21])=[C:14]([C:30]3[CH2:34][C:33]([CH2:43][C:44]([O:46]C(C)(C)C)=[O:45])([CH2:35][C:36](=[O:42])[O:37]C(C)(C)C)[O:32][N:31]=3)[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3].C(O)(C(F)(F)F)=O>>[NH:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([N:22]3[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]3)=[O:21])=[C:14]([C:30]3[CH2:34][C:33]([CH2:43][C:44]([OH:46])=[O:45])([CH2:35][C:36]([OH:42])=[O:37])[O:32][N:31]=3)[CH:13]=2)=[O:10])=[CH:51][CH:52]=1)[C:2]([NH2:4])=[NH:3]Participants
3
Procedure
A mixture of 3-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-(3-(1,1-dioxidothiomorpholin-4-yl)-3-oxopropyl)phenyl 4-carbamimidamidobenzoate (49.0 mg) and TFA (1 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and then, the pH of the residue was adjusted to about 4 by the addition of water and subsequently a saturated aqueous solution of ammonium acetate. The obtained mixture was stirred at room temperature for 3 days, and then, the obtained solid was collected by filtration and washed with water and acetone to obtain the title compound (33.1 mg).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionthe pH of the residue was adjusted to about 4 by the addition of water
- stirringThe obtained mixture was stirred at room temperature for 3 days
- filtrationthe obtained solid was collected by filtration
- washwashed with water and acetone
Sources & evidence
- ORD record
- ord-0cf18e9f15654cfaa41d069d07e7d49a
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428470B2
Reaction notes
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