Sodium Hydroxide → HCID 86594238, compound

HRID 1062683Notes

Reaction equation

HRID 1062683 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([CH:22]2[CH:26]([NH:27][C:28]([O:30][CH2:31][C:32]#[C:33][CH2:34][O:35][C:36]([NH:38][CH:39]3[CH2:43][NH:42][CH:41]([C:44]([O:46]C)=[O:45])[CH:40]3[C:48](=[O:66])[CH2:49][CH2:50][C:51]3[CH:56]=[CH:55][C:54]([CH2:57][NH:58][C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])=[CH:53][CH:52]=3)=[O:37])=[O:29])[CH2:25][NH:24][CH:23]2[C:67]([O:69]C)=[O:68])=[O:21])=[CH:14][CH:13]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:62]([O:61][C:59]([NH:58][CH2:57][C:54]1[CH:53]=[CH:52][C:51]([CH2:50][CH2:49][C:48]([CH:40]2[CH:39]([NH:38][C:36]([O:35][CH2:34][C:33]#[C:32][CH2:31][O:30][C:28]([NH:27][CH:26]3[CH2:25][NH:24][CH:23]([C:67]([OH:69])=[O:68])[CH:22]3[C:20](=[O:21])[CH2:19][CH2:18][C:15]3[CH:16]=[CH:17][C:12]([CH2:11][NH:10][C:8]([O:7][C:3]([CH3:5])([CH3:4])[CH3:6])=[O:9])=[CH:13][CH:14]=3)=[O:29])=[O:37])[CH2:43][NH:42][CH:41]2[C:44]([OH:46])=[O:45])=[O:66])=[CH:56][CH:55]=1)=[O:60])([CH3:63])([CH3:64])[CH3:65]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86594239HCID 86594239, compound

Product 1

HCID 86594238HCID 86594238, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 5 N aqueous NaOH solution (2 ml) is added dropwise to a suspension of 1,4-bis-{N-[3-(4-tert-butyloxycarbonylaminomethylphenylpropionyl)-2-methoxycarbonylpyrrolidin-4-yl]aminocarbonyloxy}2-butyne (A2, 0.6 g, 0.63 mmol) in ethanol (6 ml), and the mixture is stirred at RT for 1 h. The reaction mixture is adjusted to pH 3 with a 20% aqueous KHSO3 solution and extracted with CH2Cl2 (50 ml). The organic phase is then dried over MgSO4, filtered and concentrated in vacuo. The title compound (0.15 g) is obtained as a colorless solid. TLC, silica gel (glass plates), [Tol/Ac (6:4)], Rf=0.1.

Workup

  1. extractionextracted with CH2Cl2 (50 ml)
  2. dry with materialThe organic phase is then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c51daba95c44c9ebe19f45196823749
Source dataset
uspto-grants-2005_11
Patent number
US06962941B2

Reaction notes

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