N-(tert-butoxycarbonyl)glycine → HCID 102003297, compound
Reaction equation
N(C(OC(C)(C)C)=O)CC(O)=O.[CH3:13][C@@H:14]([C@@H:29]1[C@@:33]2([CH3:49])[CH2:34][CH2:35][CH2:36]/[C:37](=[CH:38]\[CH:39]=[C:40]3/[CH2:41][C@@H:42]([OH:48])[CH2:43][C@H:44]([OH:47])[C:45]/3=[CH2:46])/[C@@H:32]2[CH2:31][CH2:30]1)[CH2:15][C@H:16]([OH:28])[CH2:17][C:18]([OH:27])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH3:13][C@@H:14]([C@@H:29]1[C@@:33]2([CH3:49])[CH2:34][CH2:35][CH2:36]/[C:37](=[CH:38]\[CH:39]=[C:40]3/[CH2:41][C@@H:42]([OH:48])[CH2:43][C@H:44]([OH:47])[C:45]/3=[CH2:46])/[C@@H:32]2[CH2:31][CH2:30]1)[CH2:15][C:16]([CH2:17][C:18]([OH:27])([C:23]([F:24])([F:25])[F:26])[C:19]([F:22])([F:21])[F:20])=[O:28]Participants
5
Procedure
N-Boc-Gly (300 mg, 1.43 mmol) was dissolved in DCM 30 mL, next added DIPA (1 mL, 5 mmol), after several minutes added ST-232 (180 mg, 1.43 mmol), after 10 min added TBTU (550 mg, 1.71 mmol). The reaction mixture was stirred at r.t. for 1.5 h, next diluted DCM and washed with 1N HCl, 5% NaHCO3, brine and dried over MgSO4. The solvent was evaporated, and the product was purified by flash column chromatography (silica gel, DCM:MeOH 60:1 50:1 20:1), to give 200 mg (49%) of ST-233 as colorless oil.
Workup
- additionnext added DIPA (1 mL, 5 mmol)
- washnext diluted DCM and washed with 1N HCl, 5% NaHCO3, brine
- dry with materialdried over MgSO4
- customThe solvent was evaporated
- customthe product was purified by flash column chromatography (silica gel, DCM:MeOH 60:1 50:1 20:1)
Sources & evidence
- ORD record
- ord-c81d47ff845a46c79383dee8ff7bddd8
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178490B2
Reaction notes
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