Hydrochloric Acid → HCID 131732565, compound
Reaction equation
[C:1]([N:8]([CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])C)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.O.[C:38]1(=[O:44])[O:43][C:41](=[O:42])[CH2:40][CH2:39]1.CCN(C(C)C)C(C)C.Cl>>[C:13]([NH:12][CH2:11][CH2:10][N:8]([C:41]([CH2:40][CH2:39][C:38]([OH:43])=[O:44])=[O:42])[CH3:1])([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14]Participants
Procedure
Boc-NMe-CH2CH2—NH-Fmoc (520 mg, 1.31 mmol) was treated with TFA-water (15 ml, 95:5, v/v) for 1 hour at ambient temperature, when TLC analysis showed complete Boc-deprotection. TFA-water was removed under reduced pressure and the resulting oil dissolved in DCM (30 mL). To this solution, succinic anhydride (131 mg, 1.31 mmol) was added followed by DIPEA (to pH ˜10 by moist pH paper). The mixture was then stirred for 30 min. The reaction mixture was then acidified (pH=1) with HCl (1 M) and extracted with EtOAc (100 mL×3). The combined EtOAc layers were washed with brine (100 mL×2) and dried over Na2SO4. The EtOAc was removed under reduced pressure to give the title compound as a colorless oil. ES-MS (MeOH-direct infusion) Calculated MH+ (C23H26N2O5H+)=411.10, Observed MH+411.09.
Workup
- customTFA-water was removed under reduced pressure
- dissolutionthe resulting oil dissolved in DCM (30 mL)
- extractionextracted with EtOAc (100 mL×3)
- washThe combined EtOAc layers were washed with brine (100 mL×2)
- dry with materialdried over Na2SO4
- customThe EtOAc was removed under reduced pressure
Sources & evidence
- ORD record
- ord-0dc3b92c2b0345b880a39d3efb68e700
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975404B2
Reaction notes
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