Dichloromethane → 5(S)-Amino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid (N-(1-carbamoyl-1-methyl-ethyl)]-amide hydrochloride

HRID 264948Notes

Reaction equation

HRID 264948 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]([NH:14][C:15](=[O:52])[C@H:16]([CH:49]([CH3:51])[CH3:50])[CH2:17][C@H:18]([OH:48])[C@@H:19]([NH:40]C(OC(C)(C)C)=O)[CH2:20][C@@H:21]([CH:37]([CH3:39])[CH3:38])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:24]=1)([CH3:13])[CH3:12])(=[O:10])[NH2:9].[OH-].[Na+].[Cl:55]CCl>>[ClH:55].[C:8]([C:11]([NH:14][C:15](=[O:52])[C@H:16]([CH:49]([CH3:51])[CH3:50])[CH2:17][C@H:18]([OH:48])[C@@H:19]([NH2:40])[CH2:20][C@@H:21]([CH:37]([CH3:39])[CH3:38])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:24]=1)([CH3:13])[CH3:12])(=[O:10])[NH2:9]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 236270705(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(1-carbamoyl-1-methyl-ethyl)]-amide

Product 1

HCID 236264245(S)-Amino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid (N-(1-carbamoyl-1-methyl-ethyl)]-amide hydrochloride

Conditions

Temperature
0 °C

Procedure

1.5 ml of trifluoroacetic acid are added to 56 mg of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(1-carbamoyl-1-methyl-ethyl)]-amide in 1.5 ml of dichloromethane at 0° C. The mixture is stirred for a further 30 minutes at 0° C. The reaction mixture is poured onto cooled 1N sodium hydroxide and the product is extracted repeatedly with dichloromethane. The organic phases are dried, and ethereal hydrochloric acid is added. Concentration by evaporation yields the title compound: Rf (dichloromethane/methanol=8:2)=0.30; HPLC Rf =11.25; FAB-MS (M+H)+ =538.

Workup

  1. additionThe reaction mixture is poured
  2. extractionthe product is extracted repeatedly with dichloromethane
  3. customThe organic phases are dried
  4. additionethereal hydrochloric acid is added
  5. concentrationConcentration
  6. customby evaporation

Sources & evidence

ORD record
ord-eb3cfd2969074773ae0a909babe312a7
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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