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Formaldehyde → 4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-methyl-amino}-benzoic Acid Tert-butyl Ester

HRID 1755161
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HRID 1755161 반응식
[C:1]([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C=O.[C:38]([BH3-])#N.[Na+].CCOC(C)=O>CC(O)=O>[C:1]([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:14]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)[CH3:38])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 674865594-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic Acid Tert-butyl Ester

생성물 1

HCID 674863434-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-methyl-amino}-benzoic Acid Tert-butyl Ester수율 105.5%

시약·촉매·용매

1
HCID 176Acetic Acid용매

실험 절차

4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-amino}-benzoic acid tert-butyl ester (110 mg, 0.19 mmol) was dissolved in 2 mL of HOAc. paraformaldehyde (51 mg, 0.57 mmol) and sodium cyano-borohydride (36 mg, 0.57 mmol) were then added and heated to 40 C for 1 h. Cooled to RT, EtOAc (20 mL) was added and extracted water (20 mL). The organic layer was washed again with water (20 mL), dried over sodium sulfate, filtered and the organic layer was removed under reduced pressure to give a white solid (120 mg, 100%). 1H NMR showed the compound to be very clean and sufficient for the following step. LCMS (M+1=599.4)

후처리

  1. temperatureheated to 40 C for 1 h
  2. extractionextracted water (20 mL)
  3. washThe organic layer was washed again with water (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe organic layer was removed under reduced pressure

출처 및 근거

ORD 기록
ord-0d7737b6e4c0441a9e2c48411aeec3a3
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09169201B2

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