Lithium borohydride → HCID 21072811, compound

HRID 1867340Notes

Reaction equation

HRID 1867340 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].[BH4-].[Li+]>C1COCC1.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 3

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

Product 1

HCID 21072811HCID 21072811, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 232 mg (0.649 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 200 mg (0.649 mmol) of 1-(3-amino-3-methylbutyl)-4,4-diethyl-7-fluoro-1,4-dihydrobenzo[d][1,3]oxazin-2-one in absolute THF (5 mL) is stirred for 2.5 hours 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 hour. The mixture is again cooled to 5° C. and slowly diluted with 15 mL of water and 20 mL of dichloromethane. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried with sodium sulfate and concentrated by evaporation in vacuo. The residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5). Yield: 257 mg (65%); HPLC-MS: Rt=16.5 min. (method A).

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 materialThe combined organic phases are dried with sodium sulfate
  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-cc756705ac364bc0a3a81f70287e5fd8
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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