HCID 21072819, compound → HCID 21072808, compound

HRID 1867342Notes

Reaction equation

HRID 1867342 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([C:20](=[O:24])[CH:21](O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C:26]([CH3:47])([CH3:46])[CH2:27][CH2:28][N:29]1[C:34]2[C:35]([O:39][CH3:40])=[CH:36][CH:37]=[CH:38][C:33]=2[C:32]([CH2:43][CH3:44])([CH2:41][CH3:42])[O:31][C:30]1=[O:45]>>[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:24])[CH2:21][NH:25][C:26]([CH3:47])([CH3:46])[CH2:27][CH2:28][N:29]2[C:34]3[C:35]([O:39][CH3:40])=[CH:36][CH:37]=[CH:38][C:33]=3[C:32]([CH2:43][CH3:44])([CH2:41][CH3:42])[O:31][C:30]2=[O:45])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21072819HCID 21072819, compoundHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 21072808HCID 21072808, compound

Procedure

The product is prepared analogously to Example 14a starting from 5-benzyloxy-8-(2,2-dihydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1-(3-amino-3-methylbutyl)-4,4-diethyl-8-methoxy-1,4-dihydrobenzo[d][1,3]oxazin-2-one. The crude product is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5). Yield: 70 mg (18%); HPLC-MS: Rt=16.5 min. (method A).

Workup

  1. customThe product is prepared analogously to Example 14a
  2. customThe crude product is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5)

Sources & evidence

ORD record
ord-12b733f70e094c5496a4352207019f30
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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