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HCID 54419005, compound → (11S)-N-hydroxy-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide

HRID 965145
Notes
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Reaction equation

HRID 965145 reaction equation
C([O:8][NH:9][C:10](=[O:41])[CH2:11][CH:12]([C:17](=[O:40])[NH:18][C@H:19]1[CH2:37][C:36]2=[CH:38][N:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=32)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:39])[CH2:13][CH:14]([CH3:16])[CH3:15])C1C=CC=CC=1.[H][H]>C(O)C.O1CCCC1.[Pd]>[OH:8][NH:9][C:10](=[O:41])[CH2:11][CH:12]([C:17](=[O:40])[NH:18][C@H:19]1[CH2:37][C:36]2=[CH:38][N:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=32)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:39])[CH2:13][CH:14]([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 54419005HCID 54419005, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86752867(11S)-N-hydroxy-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanol
Solvent

Procedure

To a solution of the more polar stereoisomer of (11S)-N-benzyloxy-5-methyl-3-(10-oxo-1,9-diazatricyclo-[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide (90 mg) in ethanol/tetrahydrofuran (350 mL; 2:1) was added 10% palladium on charcoal (30 mg). The material was stirred with a constant stream of hydrogen gas bubbling through it. After 3 hours TLC (10% CH3OH/CH2Cl2) showed the reaction was complete. The material was filtered through a bed of celite (3×) and concentrated under reduced pressure to an almost dry residue. Methylene chloride (15 mL) was added and the material was again concentrated under reduced pressure until almost dried and then repeated. To the residue was added 3-4 drops of methanol followed by methylene chloride (15 mL). The material was stirred with cooling (ice bath) and ether (5 mL) and then hexane (2 mL) was added. A crystalline material slowly emerged and was collected by filtration to yield 50 mg of the more polar stereoisomer of (11S)-N-hydroxy-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide, m.p. 197°-201° C., [α]D23 =-85.1° (3.5 mg/1.0 mL DMSO).

Workup

  1. custombubbling through it
  2. filtrationThe material was filtered through a bed of celite (3×)
  3. concentrationconcentrated under reduced pressure to an almost dry residue
  4. additionMethylene chloride (15 mL) was added
  5. concentrationthe material was again concentrated under reduced pressure
  6. customuntil almost dried
  7. additionTo the residue was added 3-4 drops of methanol
  8. temperaturewith cooling (ice bath) and ether (5 mL)
  9. additionhexane (2 mL) was added
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-18d544ad8784469987595f3149be6917
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05773428

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes