3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinoline → 5(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

HRID 863255Notes

Reaction equation

HRID 863255 reaction equation
COCC1CC2C(=CC=CC=2)NC1.[CH2:14]([NH:18][C:19](=[O:56])[C@H:20]([CH3:55])[CH2:21][C@H:22]([OH:54])[C@@H:23]([NH:46]C(OC(C)(C)C)=O)[CH2:24][C:25]([CH3:45])([CH3:44])[CH2:26][C:27]([N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH:31]([C:39]([O:41][CH2:42]C)=O)[CH2:30]1)=[O:28])[CH2:15][CH2:16][CH3:17]>>[CH2:14]([NH:18][C:19](=[O:56])[C@H:20]([CH3:55])[CH2:21][C@H:22]([OH:54])[C@@H:23]([NH2:46])[CH2:24][C:25]([CH3:44])([CH3:45])[CH2:26][C:27]([N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH:31]([CH2:39][O:41][CH3:42])[CH2:30]1)=[O:28])[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 196976303(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinolineHCID 1317205115(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-ethoxycarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 1317205145(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Procedure

Starting from 300 mg of 3-[N-tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyloxy-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide and 465 mg of 3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinoline and subsequent reaction of the (4O,5N-isopropylidene)-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide obtained (in a manner analogous to that described in Example 1a); Rf (A)=0.38), by the method described in Example 1), the title compound is obtained as a diastereomer mixture: Rf (S)=0.31; FAB-MS: (M+H)+ =476.

Workup

  1. customobtained (in a manner analogous to

Sources & evidence

ORD record
ord-ca2ab66b6ab04c85b381fafdd47fb138
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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