Hydrochloric Acid → HCID 131720523, compound

HRID 863287Notes

Reaction equation

HRID 863287 reaction equation
Cl.[CH2:2]([NH:6][C:7](=[O:43])[C@H:8]([CH3:42])[CH2:9][C@H:10]([OH:41])[C@@H:11]([NH:33]C(OC(C)(C)C)=O)[CH2:12][C:13]1([CH2:16][C:17]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH:21]([C:29]([NH:31][CH3:32])=[O:30])[CH2:20]2)=[O:18])[CH2:15][CH2:14]1)[CH2:3][CH2:4][CH3:5].C1(C)C=CC=CC=1>O1CCOCC1>[CH2:2]([NH:6][C:7](=[O:43])[C@H:8]([CH3:42])[CH2:9][C@H:10]([OH:41])[C@@H:11]([NH2:33])[CH2:12][C:13]1([CH2:16][C:17]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH:21]([C:29]([NH:31][CH3:32])=[O:30])[CH2:20]2)=[O:18])[CH2:15][CH2:14]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 131720524HCID 131720524, compound

Product 1

HCID 131720523HCID 131720523, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2 ml of 4N hydrochloric acid in dioxane are added to 116 mg of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-6-[1-[3(R,S)-methylaminocarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonylmethyl]cyclopropyl]-2(R)-methyl-hexanoic acid (N-butyl)amide at 0° C. and the mixture is stirred for 2 h. 2 ml of toluene are added and the reaction mixture is concentrated. The oily residue is chromatographed over 10 g of silica gel (mobile phases K and L). This gives the title compound as a diastereomer mixture: Rf (P)=0.11; Rt (IV)=32.6 min; FAB-MS: (M+H)+ =487.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customThe oily residue is chromatographed over 10 g of silica gel (mobile phases K and L)

Sources & evidence

ORD record
ord-277edc14e49c4201878c2e3d70ac155c
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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