Ethyl Acetate → HCID 87680235, compound

HRID 732829Notes

Reaction equation

HRID 732829 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:39]=[CH:38][C:13]([O:14][C:15]3[C:16]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:17]=4[S:18][C:19]=3[C:20]3[CH:25]=[CH:24][C:23]([S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])=[CH:22][CH:21]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:40]([O:43]CC)(=[O:42])C>C(OCC)C>[F:32][C:29]([F:30])([F:31])[C:40]([OH:43])=[O:42].[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([O:14][C:15]3[C:16]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:17]=4[S:18][C:19]=3[C:20]3[CH:21]=[CH:22][C:23]([S:26]([C:29]([F:30])([F:31])[F:32])(=[O:27])=[O:28])=[CH:24][CH:25]=3)=[CH:38][CH:39]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 69070128HCID 69070128, compound

Product 1

HCID 87680235HCID 87680235, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve the compound of Example 96 (100 mg, 0.17 mmol) in ethyl acetate (2 mL), dilute with diethyl ether (10 mL) and place in an ice bath. Immediately add 2M HCl in diethyl ether (0.13 mL) and collect the solids on filter paper. Purify by preparative HPLC to yield 37 mg of the title compound (29%): mass spectrum (ion spray): m/z=578 (M+H).

Workup

  1. customImmediately add 2M HCl in diethyl ether (0.13 mL) and collect the solids
  2. filtrationon filter paper
  3. customPurify by preparative HPLC

Sources & evidence

ORD record
ord-9980cf2e13e74e40a865bd0eddc7393b
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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