Hydrochloric Acid → HCID 16244454、化合物

HRID 2064752ノート

反応式

HRID 2064752 の反応式
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]

参加物

8

反応物 5

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

生成物 1

HCID 16244454HCID 16244454、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-052ba936a60b4100a318775332611fa7
出典データセット
uspto-grants-2012_10
特許番号
US08288435B2

反応ノート

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