Hydrochloric Acid → HCID 69330923, compound

HRID 1351900Notes

Reaction equation

HRID 1351900 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-(triethylsilyl-oxy)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-3-phenoxypropyl]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-be1ff3af87874121a5f0fd470779de82
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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