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

HRID 1354864
ノート
印刷プレビュー

反応式

HRID 1354864 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒
HCID 13387
N-methyl-2-pyrrolidone
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-135bbcc4f1e04ef38b49fccad4f53d67
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07223759B2

反応ノート

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