Hydrochloric Acid → HCID 69330923, compound

HRID 2299687Notes

Reaction equation

HRID 2299687 reaction equation
OC[C:3]1[CH:39]=[CH:38][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([N:12](C(OC(C)(C)C)=O)[CH2:13][C@H:14]([O:23][Si](CC)(CC)CC)[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:5]=2[CH:4]=1.Cl.[C:41]([O:44][CH2:45]C)(=[O:43])[CH3:42]>>[OH:23][C@H:14]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][NH:12][CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:38]=[CH:39][C:3]([CH2:45][O:44][C:41](=[O:43])[CH3:42])=[CH:4][C:5]=2[CH2:11]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 56983775HCID 56983775, compound

Product 1

HCID 69330923HCID 69330923, compound

Procedure

A solution of N-(3-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (188 mg) in ethyl acetate (2 ml) was treated with 4N hydrogen chloride in ethyl acetate (2 ml) for 3 hours. The mixture was evaporated in vacuo and washed with diethyl ether three times. The residue was triturated in diisopropyl ether, and precipitated powder was collected by filtration to afford 6-[(2S)-2-hydroxy-3phenoxypropyl]amino-3-acetyloxymethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene (113 mg).

Workup

  1. customThe mixture was evaporated in vacuo
  2. washwashed with diethyl ether three times
  3. customThe residue was triturated in diisopropyl ether
  4. customprecipitated powder
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ae615c6868834d7bab96df1ae9cf67d5
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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