Hydrochloric Acid → HCID 67005062, compound

HRID 1513975Notes

Reaction equation

HRID 1513975 reaction equation
C(OC(=O)[N:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[O:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([F:40])[CH:37]=3)[C:32]3[C:23]2=[C:24]2[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([O:41]C)[CH:26]=[CH:25]2)=[CH:18][CH:17]=1)[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(C)(C)C.[ClH:44].B(Br)(Br)Br>ClCCl.CCOCC.C(=O)(O)[O-].[Na+].CO>[ClH:44].[ClH:44].[F:40][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[C:32]1[C:23](=[C:24]3[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([OH:41])[CH:26]=[CH:25]3)[CH:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:7][CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)=[CH:21][CH:20]=1)[O:39]2

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 11192515[4-(8-Fluoro-2-methoxy-5H-6-oxa-chrysen-5-yl)-phenyl]-(2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 67005062HCID 67005062, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve [4-(8-fluoro-2-methoxy-5H-6-oxa-chrysen-5-yl)-phenyl]-(2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester in dichloromethane (25 mL). Add a 1.0 M solution of hydrogen chloride in ether (5 mL). Concentrate in vacuo. Redissolve in dichloromethane (20 mL). Cool to 0° C. Add boron tribromide (0.238 mL, 2.52 mmol). After 3 hrs dilute with saturated aqueous sodium bicarbonate (10 mL) and methanol (10 mL). Separate the organic layer and wash the aqueous layer twice with dichloromethane. Combine the organics and dry over magnesium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography using a silica gel column eluting with a linear gradient beginning with dichloromethane and ending with 4:1 dichloromethane:methanol. Combine the product containing fractions and add 1.0 M hydrogen chloride in ether (2 mL). Concentrate in vacuo to isolate the title compound: mass spectrum (ion spray) m/z=469.2 (M+H). Purify the mixture by chiral chromatography (conditions A). The two isomers eluted with retention times of 4.02 and 5.46 minutes.

Workup

  1. concentrationConcentrate in vacuo
  2. dissolutionRedissolve in dichloromethane (20 mL)
  3. customSeparate the organic layer
  4. washwash the aqueous layer twice with dichloromethane
  5. dry with materialdry over magnesium sulfate
  6. filtrationFilter
  7. concentrationconcentrate in vacuo
  8. customPurify the residue by column chromatography
  9. washeluting with a linear gradient
  10. additioncontaining fractions
  11. additionadd 1.0 M hydrogen chloride in ether (2 mL)
  12. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-abe7b013397e4b89891897febd5ff0d5
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

Loading…