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 725645Notes

Reaction equation

HRID 725645 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 Rt =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-5308d92f914441999204a4730cb886f2
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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