Benzyl Alcohol → HCID 67393803, compound

HRID 910479Notes

Reaction equation

[N:1]([C:4]([CH3:54])([CH3:53])[CH2:5][C@@H:6]1[NH:11][CH2:10][C@H:9]([O:12][CH:13]([C:24]2[CH:25]=[CH:26][C:27]3[O:32][CH2:31][CH2:30][N:29]([CH2:33][CH2:34][CH2:35][O:36][CH3:37])[C:28]=3[CH:38]=2)S(C2C=CC(C)=CC=2)(=O)=O)[C@@H:8]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][O:46][CH2:47][C@H:48]([O:50][CH2:51][CH3:52])[CH3:49])=[CH:41][CH:40]=2)[CH2:7]1)=[C:2]=[O:3].[CH2:55](O)C1C=CC=CC=1>>[CH2:51]([O:50][C@H:48]([CH3:49])[CH2:47][O:46][CH2:45][C:42]1[CH:41]=[CH:40][C:39]([C@@H:8]2[C@@H:9]([O:12][CH2:13][C:24]3[CH:25]=[CH:26][C:27]4[O:32][CH2:31][CH2:30][N:29]([CH2:33][CH2:34][CH2:35][O:36][CH3:37])[C:28]=4[CH:38]=3)[CH2:10][NH:11][C@@H:6]([CH2:5][C:4]([NH:1][C:2](=[O:3])[CH3:55])([CH3:53])[CH3:54])[CH2:7]2)=[CH:44][CH:43]=1)[CH3:52]

Participants

Reactant 2

HCID 244Benzyl Alcohol

HCID 87381592HCID 87381592, compound

Product 1

HCID 67393803HCID 67393803, compound

Conditions

Temperature: 115 °C

Procedure

A mixture of 1.0 mmol of 6-[(3R,4R,6R)-6-(2-isocyanato-2-methyl-propyl)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-1-(toluene-4-sulfonyl)-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl) -3,4-dihydro-2H-benzo[1,4]oxazine and 20.0 mmol of benzyl alcohol is heated at 115° C. for 14 h. The reaction mixture is directly purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on its Rf value.

Workup

customThe reaction mixture is directly purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record: ord-e69d8102da5246608eba7b06f2a95bcc
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022069B2

Reaction notes

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