Acetyl chloride → HCID 42633025, compound

HRID 1674684Notes

Reaction equation

C(OC([N:8]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[C:20]=3[CH:30]=2)[C@@H:11]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][O:38][CH2:39][C@H:40]([O:42][CH2:43][CH3:44])[CH3:41])=[CH:33][CH:32]=2)[C@H:10]([CH2:45][NH2:46])[CH2:9]1)=O)(C)(C)C.[C:47](Cl)(=[O:49])[CH3:48]>>[CH2:43]([O:42][C@H:40]([CH3:41])[CH2:39][O:38][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([C@@H:11]2[C@@H:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]4[O:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[C:20]=4[CH:30]=3)[CH2:13][NH:8][CH2:9][C@H:10]2[CH2:45][NH:46][C:47](=[O:49])[CH3:48])=[CH:32][CH:33]=1)[CH3:44]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 67336412HCID 67336412, compound

Product 1

HCID 42633025HCID 42633025, compound

Procedure

Analogously to example 2a, (3R,4R,5R)-3-aminomethyl-4-[4-((R)-2-ethoxypropoxy-methyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 6a) and acetyl chloride are used to afford the title compound as a yellow oil oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.12 (EtOAc); Rt=4.87 (gradient I).

Sources & evidence

ORD record: ord-c990cbf4fa9e44b0b6afb3ff87563ca1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003640B2

Reaction notes

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