Phosphate → HCID 10250534, compound

HRID 892002Notes

Reaction equation

HRID 892002 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][N:10]1[C@@H:14]([CH2:15][O:16][C:17](=[S:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12][C:11]1=[O:28].P([O-])([O-])([O-])=O>CC#N>[O:28]=[C:11]1[CH2:12][CH2:13][C@H:14]([CH2:15][O:16][C:17](=[S:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:10]1[CH2:9][C:8]#[C:7][CH2:6][CH2:5][CH2:4][C:3]([OH:29])=[O:2]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 10341866HCID 10341866, compound

Product 1

HCID 10250534HCID 10250534, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Rabbit liver esterase (134 units/mg, 1 mg), ester 5 (6.0 mg, 0.015 mmol), MeCN (0.1 mL) and pH 7.2 phosphate buffer (2.0 mL) were stirred together at rt overnight. MeCN (5.0 mL) was added and the reaction was concentrated in vacuo. Purification of the residue by flash column chromatography on silica (100% CH2Cl2→2% MeOH/CH2Cl2, gradient) afforded 3.2 mg (55%) of the title compound (6).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customPurification of the residue by flash column chromatography on silica (100% CH2Cl2→2% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-7688c27b240e42fa86defe1f50b3295e
Source dataset
uspto-grants-2006_02
Patent number
US07005442B2

Reaction notes

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