Phosphate → HCID 18376061, compound

HRID 2117517Notes

Reaction equation

HRID 2117517 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 mixture 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 product was extracted into CH2Cl2 (3x). 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 product was extracted into CH2Cl2 (3x)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1cfe66fedb214c3c84dd0c1a8297378f
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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