Acetic Acid → HCID 58687907, 화합물

HRID 1988573노트

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HRID 1988573 반응식
[N:1]1([C:7]2[O:12][C:11]([C:13]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:14]=3[S:15][C:16]3[CH:17]=[CH:18][C:19]([CH:27]=[O:28])=[CH:20][C:21]=3[CH2:22]4)=[CH:10][C:9](=[O:29])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[OH:28][CH2:27][C:19]1[CH:20]=[C:21]2[C:16]([S:15][C:14]3[C:13]([C:11]4[O:12][C:7]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:8][C:9](=[O:29])[CH:10]=4)=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22]2)=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 176Acetic Acid2회HCID 5003444Sodium cyanoborohydrideHCID 58687906HCID 58687906, 화합물

생성물 1

HCID 58687907HCID 58687907, 화합물수율 84%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthene-2-carbaldehyde (2)(0.392 g, 0.97 mmol) in ethanol (7 mL) at room temperature was added sodium cyanoborohydride (121 mg, 1.93 mmol), followed by the addition of acetic acid (1 mL). After 5 hours, a second addition of acetic acid (1 mL) was made. After a further 12 hours, the excess borohydride was quenched with acetone. After evaporation in vacuo, saturated NaHCO3 was added, followed by extraction into dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The brown coloured solid was dried under vacuum at 50° C. to give the crude title compound (0.332 g, 84%) which was used without any further purification. m/z (LC-MS, ESP), RT=3.09 min, (M++1)=408.3

후처리

  1. waitAfter a further 12 hours
  2. customthe excess borohydride was quenched with acetone
  3. customAfter evaporation in vacuo, saturated NaHCO3
  4. additionwas added
  5. extractionfollowed by extraction into dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe brown coloured solid was dried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-3a6ec440699d49bead9bc9ecb44e0a4c
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642254B2

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