Hydrochloric Acid → HCID 118101229, compound
Reaction equation
[CH:1]1([C@H:4]([OH:27])[CH2:5][O:6][C:7]2[C:22]([F:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:8]=2[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12]C(C)(C)C)[CH2:3][CH2:2]1.Cl.O1CCOCC1.[CH2:35](OC(ON1C(=O)CCC1=O)=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)C(C)C)(C)C>CCOC(C)=O>[CH:1]1([C@H:4]([OH:27])[CH2:5][O:6][C:7]2[C:22]([F:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:8]=2[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:3][CH2:2]1Participants
7
Procedure
To 21D (88 mg, 0.229 mmol) in EtOAc (2 mL) was added 4.0 M HCl in dioxane (1.5 mL, 6.00 mmol). The mixture was stirred rt for 1 h, concentrated. The residue was dissolved in DMF (10 ml). N-(benzyloxycarbonyloxy) succinimide (62.8 mg, 0.252 mmol) was added, followed by N,N-diisopropylethylamine (0.120 mL, 0.687 mmol). The mixture was stirred rt for 16 h, then was quenched with water, extracted with EtOAc (3×30 ml). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0-60% EtOAc in hexane) to give 21E (99 mg, 103% yield). MS (ESI) m/z: 419.3 (M+H)+.
Workup
- concentrationconcentrated
- dissolutionThe residue was dissolved in DMF (10 ml)
- stirringThe mixture was stirred rt for 16 h
- customwas quenched with water
- extractionextracted with EtOAc (3×30 ml)
- washThe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude product was purified by flash chromatography (0-60% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-9e31e9fd72a14d0fa92d919dcf858a48
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174974B2
Reaction notes
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