2,2-Dimethoxypropane → HCID 86752106, compound

HRID 863288Notes

Reaction equation

HRID 863288 reaction equation
[CH2:1]([NH:5][C:6](=[O:35])[C@H:7]([CH3:34])[CH2:8][C@H:9]([OH:33])[C@@H:10]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:11][C:12]1([CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4].CO[C:38](OC)([CH3:40])[CH3:39].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([NH:5][C:6](=[O:35])[C@H:7]([CH3:34])[CH2:8][C@@H:9]1[O:33][C:38]([CH3:40])([CH3:39])[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:10]1[CH2:11][C:12]1([CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86752107HCID 86752107, compound

Product 1

HCID 86752106HCID 86752106, compound

Procedure

The 5(S)-tert-butoxycarbonylamino-6-[1-(2-benzyloxyethyl)cyclopropyl]-4(S)-hydroxy-2(R)-methyl-hexanoic acid (N-butyl)amide thus obtained is reacted with dimethoxypropane and p-toluenesulfonic acid hydrate in a manner analogous to that described in Example 1 d) and the product is purified by means of FC over 80 g of silica gel (mobile phase C). This gives the title compound as the pure diastereomer: Rf (A)=0.58,

Workup

  1. customthat described in Example 1 d
  2. customis purified by means of FC over 80 g of silica gel (mobile phase C)

Sources & evidence

ORD record
ord-5442c21595ff48b886caa8427b5c2927
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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