Acetyl chloride → HCID 66876965, compound

HRID 1863981Notes

Reaction equation

HRID 1863981 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]3[O:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[C:23]=3[CH:33]=2)[C@@H:14]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][O:41][CH2:42][C@@H:43]([CH3:47])[CH2:44][O:45][CH3:46])=[CH:36][CH:35]=2)[C@H:13]([CH2:48][OH:49])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:50](Cl)(=[O:52])[CH3:51]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]3[O:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[C:23]=3[CH:33]=2)[C@@H:14]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][O:41][CH2:42][C@@H:43]([CH3:47])[CH2:44][O:45][CH3:46])=[CH:36][CH:35]=2)[C@H:13]([CH2:48][O:49][C:50](=[O:52])[CH3:51])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 66877910HCID 66877910, compound

Product 1

HCID 66876965HCID 66876965, compound

Procedure

Analogously to Example 2a, (3S,4R,5R)-3-hydroxymethyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H -benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester (Example 1a) and acetyl chloride are used to afford the title compound as a colorless oil. Rf=0.20 (EtOAc-heptane 1:1); Rt=5.69 (gradient I).

Sources & evidence

ORD record
ord-5d5fa672a0cf471196d594f59046f079
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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