Triethylamine → HCID 178480557, compound

HRID 1670646Notes

Reaction equation

HRID 1670646 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:34]=1)[O:7][CH2:8][C:9]1[CH:33]=[CH:32][CH:31]=[CH:30][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C@H:20]2[CH2:24][N:23]([CH3:25])[CH2:22][C@@H:21]2[OH:26])=[C:15]([N+:27]([O-])=O)[CH:14]=1.C(N(CC)CC)C.C1C=CC(O[C:49](OC2C=CC=CC=2)=[N:50][C:51]#[N:52])=CC=1>C(O)(C)C.[Pt]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:34]=1)[O:7][CH2:8][C:9]1[CH:33]=[CH:32][CH:31]=[CH:30][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]2[N:19]([C@@H:20]3[C@@H:21]([OH:26])[CH2:22][N:23]([CH3:25])[CH2:24]3)/[C:49](=[N:50]/[C:51]#[N:52])/[NH:27][C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 57748760(3S,4s)-4-(4-((E)-(3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)methyl)-2-nitrophenylamino)-1-methylpyrrolidin-3-ol

Product 1

HCID 178480557HCID 178480557, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of (3S,4S)-4-(4-((E)-(3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)methyl)-2-nitrophenylamino)-1-methylpyrrolidin-3-ol (3.10 mmol, 1.43 g) in isopropanol (85 mL) and triethylamine (9.3 mmol, 1.30 mL) add 5% Pt/C (420 mg) and hydrogenate at 50 psi for 1.5 h. Filter through a plug of diatomaceous earth and wash with isopropanol (50 mL). Add diphenyl cyanocarbonimidate (3.1 mmol, 0.74 g) and stir at room temperature overnight, then heat to reflux for 3 h. Remove the solvent and purify the residue by column chromatography eluting with a gradient from 0% to 20% methanol in methylene chloride to give the title compound as a light brown solid (955 mg, 57%). [α]D23+13.8 (c 0.17, CH3OH); ESI MS m/z 482 [M+H]+.

Workup

  1. filtrationFilter through a plug of diatomaceous earth
  2. washwash with isopropanol (50 mL)
  3. temperatureheat
  4. temperatureto reflux for 3 h
  5. customRemove the solvent
  6. custompurify the residue by column chromatography
  7. washeluting with a gradient from 0% to 20% methanol in methylene chloride

Sources & evidence

ORD record
ord-9c65b4c7f26645a3a641163d5f4d62b2
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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