2-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acid → 4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenyl N-(tert-butoxycarbonyl)glycylglycinate
Reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[F:15])[C:8]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]([O:27][C:28]([NH:30][CH2:31][C:32]([NH:34][CH2:35][C:36](O)=[O:37])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:23]([O:27][C:28]([NH:30][CH2:31][C:32]([NH:34][CH2:35][C:36]([O:22][C:19]1[CH:18]=[CH:17][C:16]([C:8]2[C:9]3[C:14](=[C:13]([F:15])[CH:12]=[CH:11][CH:10]=3)[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=2)=[CH:21][CH:20]=1)=[O:37])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenol (0.30 g, 1.0 mmol), N-(tert-butoxycarbonyl)glycylglycine (0.232 g, 1.0 mmol), N,N-dicylohexylcarbodiimide (0.206 g, 1.0 mmol) and DMAP (0.122 g, 1.0 mmol) in 10 mL of CH2Cl2 was stirred overnight at ambient temperature. The reaction mixture was diluted with CH2Cl2 and filtered through a plug of silica gel. The gel was rinsed with additional CH2Cl2. The combined filtrates were concentrated in vacuo to give 0.35 g to the title compound as a white solid, mp 103–104° C.;
Workup
- filtrationfiltered through a plug of silica gel
- washThe gel was rinsed with additional CH2Cl2
- concentrationThe combined filtrates were concentrated in vacuo
Sources & evidence
- ORD record
- ord-532644139a504b3289f3d36f359c17ee
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241791B2
Reaction notes
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