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Hydrochloric Acid → (4-Amino-3-benzyloxyphenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 1354864
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HRID 1354864 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:36])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24]C(=O)C)=[C:20]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl>CO.CN1C(=O)CCC1.O1CCOCC1.CCOC(C)=O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:36])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 313Hydrochloric AcidHCID 58865050(4-Acetylamino-3-benzyloxy-phenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

생성물 1

HCID 58865047(4-Amino-3-benzyloxyphenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester수율 46.7%

시약·촉매·용매 4

HCID 887Methanol용매HCID 8857Ethyl Acetate용매
HCID 13387
N-methyl-2-pyrrolidone
용매
HCID 312751,4-Dioxane용매

실험 절차

(4-Acetylamino-3-benzyloxy-phenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (420) (3 g, 6.28 mmol) was dissolved in a mixture of MeOH (15 mL) and NMP (10 mL). 4.0 M HCl in dioxane (20 mL) was added and the mixture was refluxed for 40 h. LC-MS indicated complete de-protection at this point. The mixture was diluted with EtOAc (200 mL), washed with saturated aqueous NaHCO3 (3×300 mL), water (100 mL) and brine (100 mL) via extraction, dried over MgSO4 and upon concentration under reduced pressure, a precipitate formed. Collection by filtration under reduced pressure followed by drying under high vacuum for 16 h gave the desired product (65) as a beige/pink powder (1.28 g, 2.93 mmol, 46.7% yield). LC-MS (ESI): (exact mass: 436.18) m/e=437.2 [M+1]+ (100%), 873.5 [2M+1]+ (100%).

후처리

  1. temperaturethe mixture was refluxed for 40 h
  2. washwashed with saturated aqueous NaHCO3 (3×300 mL), water (100 mL) and brine (100 mL) via extraction
  3. dry with materialdried over MgSO4 and upon concentration under reduced pressure
  4. customa precipitate formed
  5. customCollection
  6. filtrationby filtration under reduced pressure
  7. customby drying under high vacuum for 16 h

출처 및 근거

ORD 기록
ord-135bbcc4f1e04ef38b49fccad4f53d67
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07223759B2

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