Hydrochloric Acid → HCID 18433613, compound

HRID 2187875Notes

Reaction equation

HRID 2187875 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[NH:19]C(OC(C)(C)C)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CCOC(C)=O>[NH2:19][C:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:18]=2)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18433467HCID 18433467, compound

Product 1

HCID 18433613HCID 18433613, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-benzyloxy-1-(tert-butoxycarbonylamino) naphthalene, as described above in Step I, (100 mg, 0.29 mmol) in EtOAc (10 mL) at 0° C. was saturated with HCl (g). After 15 min, the mixture was concentrated in vacuo. The residue was partitioned between saturated aqueous Na2CO3 (5 mL) and CH2Cl2 (10 mL). The aqueous layer was extracted further with CH2Cl2 (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield the desired amine as a pale solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous Na2CO3 (5 mL) and CH2Cl2 (10 mL)
  3. extractionThe aqueous layer was extracted further with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-464f1f2eee6c430884d590b6e255e5ed
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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