Phosphate → HCID 18376061, compound

HRID 2300469Notes

Reaction equation

HRID 2300469 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[CH:23][CH:22]=1)[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)(=[O:13])=[O:12].P([O-])([O-])([O-])=O>CC(C)=O>[N:27]1([C:24]2[CH:23]=[CH:22][C:21]([CH2:20][N:10]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:26][CH:25]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

4

Reactant 2

HCID 1061PhosphateHCID 54199818HCID 54199818, compound

Product 1

HCID 18376061HCID 18376061, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixutre of 7-[(4-imidazol-1-yl-benzyl)-(pyridine-2-sulfonyl)-amino]-heptanoic acid methyl ester (52 mg), porcine pancreas lipase (81 mg), acetone (1 mL), and phosphate buffer (pH=7, 5 mL) was stirred at room temperature for 20 h. The produce was extracted into CH2Cl2 (3×). The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound (44 mg). 1H NMR (400 MHz, CD3OD) δ 8.71 (m, 1H), 8.24 (s, 1H), 8.07-7.98 (m, 2H), 7.64-7.54 (m, 6H), 7.19 (s, 1H), 4.57 (s, 2H), 3.29 (t, 2H), 2.15 (t, 2H), 1.41 (m, 2H), 1.33 (m, 2H), 1.13 (m, 4H).

Workup

  1. extractionThe produce was extracted into CH2Cl2 (3×)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b370b321648d4b23bef09b08d5e059b6
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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