Tetrahydrofuran → HCID 21072811, compound

HRID 1372919Notes

Reaction equation

HRID 1372919 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:20](=[O:26])[CH:21](OCC)O)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]([CH3:48])([CH3:47])[CH2:29][CH2:30][N:31]1[C:36]2[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=2[C:34]([CH2:44][CH3:45])([CH2:42][CH3:43])[O:33][C:32]1=[O:46].C1COCC1.[BH4-].[Li+]>O.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:26])[CH2:21][NH:27][C:28]([CH3:48])([CH3:47])[CH2:29][CH2:30][N:31]2[C:36]3[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=3[C:34]([CH2:44][CH3:45])([CH2:42][CH3:43])[O:33][C:32]2=[O:46])[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21072818HCID 21072818, compoundHCID 22063474HCID 22063474, compound

Product 1

HCID 21072811HCID 21072811, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 232 mg (0.649 mmol) 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 200 mg (0.649 mmol) 1-(3-amino-3-methyl-butyl)-4,4-diethyl-7-fluoro-1,4-dihydro-benzo[d][1,3]oxazin-2-one in abs. THF (5 mL) is stirred for 2.5 h at RT. The mixture is cooled to 5° C., combined with 60 mg (2.755 mmol) lithium borohydride, heated to RT and stirred for 1 h. The mixture is again cooled to 5° C. and slowly diluted with 15 ml water and 20 mL dichloromethane. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined org. phases are dried with sodium sulphate and concentrated by evaporation in vacuo. The residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5).

Workup

  1. temperatureheated to RT
  2. temperatureThe mixture is again cooled to 5° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialphases are dried with sodium sulphate
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5)

Sources & evidence

ORD record
ord-1ff931f201fe4d84abd6d0b62eaba292
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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