Hydrochloric Acid → HCID 69537261, compound

HRID 2220380Notes

Reaction equation

HRID 2220380 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:30][C@H:31]([OH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[C:19]([S:26][CH:27]([CH3:29])[CH3:28])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:39][S:40]([NH2:43])(=[O:42])=[O:41].Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C=O.CN(C)C1C=CN=CC=1>[OH:38][C@H:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:30][N:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])=[O:24])=[C:19]([S:26][CH:27]([CH3:29])[CH3:28])[CH:18]=2)=[CH:15][CH:16]=1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69102595HCID 69102595, compound

Product 1

HCID 69537261HCID 69537261, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(isopropylthio)-4-biphenycarboxylic acid (131 mg) in N,N-dimethylformamide (2.6 ml) were added methanesulfonamide (24.9 mg), 4-(dimethylamino)pyridine (43.7 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (91.4 mg) at room temperature and the mixture was stirred at the same temperature for 72 hours. The mixture was poured into aqueous hydrochloric acid solution (0.3N) and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/3) to give tert-butyl [(2R)-2-hydroxy-2-phenylethyl](2-[3′-(isopropylthio)-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]ethyl]-carbamate (10 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-8748cde452e24f20b38d7a6560f4c365
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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