Phosphate → HCID 68570419, compound

HRID 1176553Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH:18]2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([O:42][CH2:43][CH2:44][C:45]([O:47]C)=[O:46])[CH:36]=2)=[CH:13][CH:12]=1.C(OC(C)C)(C)C.P([O-])([O-])([O-])=O>CS(C)=O>[C:45]([CH2:44][CH2:43][O:42][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][C:38]=1[CH3:41])[CH2:34][O:33][CH:18]1[CH:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]3[CH:49]=[CH:50][CH:51]=[CH:52][C:3]=3[O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:19]1)([OH:47])=[O:46]

Participants

Conditions

Temperature: 35 °C

Procedure

The mixture of 0.527 g of benzyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[3-(2-methoxycarbonylethoxy)-4-methylbenzyloxy]piperidine-1-carboxylate, 20 ml of diisopropyl ether, 0.20 ml of dimethyl sulphoxide and 100 ml of pH 7.0 phosphate buffer is admixed with 15 ml of Novozyme 398 (Novo Nordisk) and stirred at 35° C. over 120 hours. The reaction mixture is extracted repeatedly with tetrahydrofuran and the organic phases are concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.10 (1:1 EtOAc-heptane); Rt=5.57.

Workup

extractionThe reaction mixture is extracted repeatedly with tetrahydrofuran
concentrationthe organic phases are concentrated by evaporation

Sources & evidence

ORD record: ord-e7be0e729afc4db5a828f98517fe1692
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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