Hydrochloric Acid → HCID 16244454, 화합물

HRID 2064752노트

반응식

HRID 2064752 반응식
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12]([C:14]1[C:23]2[O:22][CH2:21][C:20](=O)[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13].[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH3:10][O:11][C:12]([C:14]1[C:23]2[O:22][CH2:21][CH2:20][NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23770643Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

생성물 1

HCID 16244454HCID 16244454, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
5 °C

실험 절차

Boron trifluoride diethyl etherate (10.1 mmol) is added dropwise to a mixture of 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester (4.83 mmol) in THF (12 mL) to keep the temperature below 5° C. After 20 min NaBH4 (10.1 mmol) is added and the mixture is stirred at 5° C. for 60 min. EtOAc (6.0 mL) and hydrochloric acid (1.0 M, 6.0 mL) are added dropwise. The mixture is made basic by addition of sat. aq. NaHCO3 solution, the layers are separated and the aq. layer is extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by CC (heptane to heptane/EtOAc 3/7). LC-MS: tR=0.69 min; [M+H]+=194.0.

후처리

  1. customthe temperature below 5° C
  2. customthe layers are separated
  3. extractionthe aq. layer is extracted with EtOAc
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-052ba936a60b4100a318775332611fa7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288435B2

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