Hydrochloric Acid → HCID 25255503, compound

HRID 1014577Notes

Reaction equation

HRID 1014577 reaction equation
Cl.[CH:2]1([CH2:9][O:10][C:11]2[CH:12]=[C:13]([C:17](=[O:28])[CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>CCOC(C)=O.C(OCC)C>[NH2:20][CH2:19][CH2:18][C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH:2]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:12]=1)=[O:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67316290Tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-oxopropylcarbamate

Product 1

HCID 25255503HCID 25255503, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

HCl gas was bubbled for 1-2 min through an ice-cold solution of tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-oxopropylcarbamate (0.495 g, 1.318 mmol) in EtOAc (ca. 20 mL). The reaction mixture was warmed to room temperature. After stirring overnight, the mixture was diluted with diethyl ether (ca. 30 mL). The white solid was collected by filtration, washed with diethyl ether and hexanes and dried under vacuum for 4 h. Example 16 was isolated as a white solid. Yield (0.285 g, 69%): 1H NMR (400 MHz, DMSO-d6) δ 8.05 (br s, 3H), 7.52 (dt, J=8.0, 1.2 Hz, 1H), 7.44 (t, J=8.0 Hz, 1H), 7.40 (t, J=2.4 Hz, 1H), 7.23 (ddd, J=8.4, 2.8, 1.2 Hz, 1H), 3.81 (d, J=6.4 Hz, 2H), 3.41 (t, J=6.4 Hz, 2H), 3.10 (q, J=5.6 Hz, 2H), 1.88-1.95 (m, 1H), 1.76-1.83 (m, 2H), 1.61-1.69 (m, 2H), 1.38-1.59 (m, 6H), 1.22-1.31 (m, 2H).*

Workup

  1. filtrationThe white solid was collected by filtration
  2. washwashed with diethyl ether and hexanes
  3. customdried under vacuum for 4 h
  4. customExample 16 was isolated as a white solid
  5. customYield (0.285 g, 69%)

Sources & evidence

ORD record
ord-725a7935eac94647b7bdd76b07b3c39d
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

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