Phosphate → HCID 10250534, compound

HRID 1582177Notes

Reaction equation

HRID 1582177 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-d14b5d1c2d7e47858f9c1015f38e9843
Source dataset
uspto-grants-2004_05
Patent number
US06734201B1

Reaction notes

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