Ethyl Acetate → HCID 86595797, compound

HRID 586654Notes

Reaction equation

HRID 586654 reaction equation
[CH3:1][C:2]12[C:8]([CH3:10])([CH3:9])[C:5]([C:11]([O:13][CH2:14][C@H:15]3[C@@H:17]([CH2:18][O:19][CH3:20])[C@@:16]3([CH3:35])[C:21]3[CH:30]=[CH:29][C:28]4[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=4[CH:22]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:36].[CH3:37][C:38]12[C:44]([CH3:46])([CH3:45])[C:41]([C:47]([O:49][CH2:50][C@@H:51]3[C@H:53]([CH2:54][O:55][CH3:56])[C@:52]3([CH3:71])[C:57]3[CH:66]=[CH:65][C:64]4[C:63]([CH3:68])([CH3:67])[CH2:62][CH2:61][C:60]([CH3:70])([CH3:69])[C:59]=4[CH:58]=3)=[O:48])([CH2:42][CH2:43]1)[O:40][C:39]2=[O:72].COCC1[C@@H](CO)C1(C)C1C=CC2C(C)(C)CCC(C)(C)C=2C=1.CCOC(C)=O>CCCCCC>[CH3:1][C:2]12[C:8]([CH3:9])([CH3:10])[C:5]([C:11]([O:13][CH2:14][C@H:15]3[C@H:17]([CH2:18][O:19][CH3:20])[C@@:16]3([CH3:35])[C:21]3[CH:30]=[CH:29][C:28]4[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=4[CH:22]=3)=[O:12])([CH2:6][CH2:7]1)[O:4][C:3]2=[O:36].[CH3:37][C:38]12[C:44]([CH3:45])([CH3:46])[C:41]([C:47]([O:49][CH2:50][C@@H:51]3[C@@H:53]([CH2:54][O:55][CH3:56])[C@:52]3([CH3:71])[C:57]3[CH:66]=[CH:65][C:64]4[C:63]([CH3:68])([CH3:67])[CH2:62][CH2:61][C:60]([CH3:70])([CH3:69])[C:59]=4[CH:58]=3)=[O:48])([CH2:42][CH2:43]1)[O:40][C:39]2=[O:72]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 69740307HCID 69740307, compoundHCID 86595795HCID 86595795, compoundHCID 86595796HCID 86595796, compound

Product 2

HCID 86595797HCID 86595797, compoundYield 36%HCID 86759822HCID 86759822, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following a procedure similar to that for the preparation of Intermediates 8a and 9a while using Intermediate 7a as the starting material and 10% EtOAc in hexane as normal phase HPLC eluent afforded Intermediate 10a (46 mg, 36% yield) and Intermediate 11a (45 mg, 36% yield) from 7a as colorless oils:

Sources & evidence

ORD record
ord-a802f036819b4923bd34ee3fb862968c
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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