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

HRID 1354864Notes

Reaction equation

HRID 1354864 reaction equation
[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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Procedure

(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%).

Workup

  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

Sources & evidence

ORD record
ord-135bbcc4f1e04ef38b49fccad4f53d67
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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