HCID 21072820, compound → HCID 21072809, compound

HRID 1867338Notes

Reaction equation

HRID 1867338 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.Cl.[NH2:26][C:27]([CH3:48])([CH3:47])[CH2:28][CH2:29][N:30]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[C:33]([CH2:43][CH2:44][CH3:45])([CH2:40][CH2:41][CH3:42])[O:32][C:31]1=[O:46]>CCOC(C)=O>[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:26][C:27]([CH3:47])([CH3:48])[CH2:28][CH2:29][N:30]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[C:33]([CH2:43][CH2:44][CH3:45])([CH2:40][CH2:41][CH3:42])[O:32][C:31]2=[O:46])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21072820HCID 21072820, compoundHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 21072809HCID 21072809, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product is prepared analogously to Example 12a starting from 5-benzyloxy-8-(2,2-dihydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1-(3-amino-3-methylbutyl)-4,4-dipropyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one hydrochloride. The crude product is dissolved in EtOAc, washed with 5% aqueous NaOH solution, and purified by column chromatography (silica gel, dichloromethane/MeOH 98:2→90:10). Yield: 170 mg (49%); HPLC-MS: Rt=18.9 min. (method A).

Workup

  1. customThe product is prepared analogously to Example 12a
  2. washwashed with 5% aqueous NaOH solution
  3. custompurified by column chromatography (silica gel, dichloromethane/MeOH 98:2→90:10)

Sources & evidence

ORD record
ord-c2cec4324e4246a28839c2ffb3a4c561
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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