Hydrochloric Acid → HCID 86598287, compound

HRID 902660Notes

Reaction equation

HRID 902660 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.O[C:16]1[CH:17]=[C:18]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.[Cl:28][C:29]1[C:30]([C:55]([F:58])([F:57])[F:56])=[C:31]([CH:52]=[CH:53][CH:54]=1)[CH2:32][N:33]([CH2:38][CH:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:34][CH2:35][CH2:36][OH:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)C>[ClH:28].[Cl:28][C:29]1[C:30]([C:55]([F:56])([F:57])[F:58])=[C:31]([CH:52]=[CH:53][CH:54]=1)[CH2:32][N:33]([CH2:38][CH:39]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:34][CH2:35][CH2:36][O:37][C:19]1[CH:20]=[CH:21][CH:16]=[CH:17][C:18]=1[S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 211278523-hydroxy-N,N-dimethylbenzenesulfonamideHCID 69252393HCID 69252393, compound

Product 1

HCID 86598287HCID 86598287, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

DIAD (48 uL, 0.24 mmol) was added dropwise to a RT solution of 3-hydroxy-N,N,-dimethyl-benzenesulfonamide (0.040 g, 0.2 mmol), 3-[(3-chloro-2-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol (0.088 g, 0.2 mmol) and triphenylphosphine (0.063 g, 0.24 mmol). The mixture was stirred for 48 at rt than was concentrated and purified by reverse phase HPLC to provide a solid which was dissolved in CH2Cl2 and treated with excess 4M HCl in diethyl ether. The mixture was concentrated to provide 35 mg (25%) of the title compound. MS (ESI) 632 (M+H+).

Workup

  1. concentrationthan was concentrated
  2. custompurified by reverse phase HPLC
  3. customto provide a solid which
  4. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-cd292b5bf9574833af96d6bcea53a7c2
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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