Citric Acid → HCID 57936499, compound

HRID 1434859Notes

Reaction equation

HRID 1434859 reaction equation
C([Si]([O:11][CH2:12][C@@H:13]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(C(C)C)C(C)C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:19]([O:18][C:16]([NH:15][CH2:14][C@H:13]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)[CH2:12][OH:11])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 57936539HCID 57936539, compound

Product 1

HCID 57936499HCID 57936499, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. mixture of (2S)-3-(t-butoxycarbonylamino)-2-(3,4-dimethoxybenzyloxy)propyl triisopropylsilyl ether (1 g, 2.01 mmol) and THF (5 mL) was added 1 M TBAF/THF (2.11 mL, 2.11 mmol). The reaction was stirred for 1 h and satd citric acid (5 mL) and CH2Cl2 were added. The organic layer was partitioned, concentrated, and chromatographed (CH2Cl2 to 50% EtOAc/CH2Cl2) to give the title compound (545 mg, 80%).

Workup

  1. customThe organic layer was partitioned
  2. concentrationconcentrated
  3. customchromatographed (CH2Cl2 to 50% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-0a3e28abf2264b81910840e2701249bb
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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