Toluene → HCID 69646185, compound

HRID 1684753Notes

Reaction equation

HRID 1684753 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([NH:15][C@H:16]([C@@H:36]([OH:49])[CH2:37][C@H:38]([C:42](=[O:48])[NH:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:39]([CH3:41])[CH3:40])[CH2:17][C@@H:18]([CH:33]([CH3:35])[CH3:34])[CH2:19][NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28]COC)=O)(C)(C)C.C1(C)C=CC=CC=1>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:15][C@H:16]([C@@H:36]([OH:49])[CH2:37][C@H:38]([C:42](=[O:48])[NH:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:39]([CH3:40])[CH3:41])[CH2:17][C@@H:18]([CH:33]([CH3:34])[CH3:35])[CH2:19][NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57179378HCID 57179378, compound

Product 1

HCID 69646185HCID 69646185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 ml) is added at 0° C., with stirring, to a solution of (2S,4S,5S,7S)-N-[4-(tert-butoxycarbonyl)amino-7-butylcarbamoyl-5-hydroxy-2-isopropyl-8-methyl-nonyl]-2-(methoxymethoxy)-benzamide (46 mg) in dichloromethane (2 ml). When the reaction is complete (after approximately 30 minutes), toluene (2 ml) is added and the reaction mixture is concentrated. The crude product obtained after briefly drying under a high vacuum is purified by FC on 6 g of silica gel (eluant Q), and (2S,4S,5S,7S)-N-(4-amino-7-butylcarbamoyl-5-hydroxy-2-isopropyl-8-methyl-nonyl)-2-hydroxy-benzamide trifluoroacetate is obtained: Rf (W)=0.34. HPLC Rt =12.1 min. MS(FAB) m/e 450 (M+ +1).

Workup

  1. additionis added
  2. concentrationthe reaction mixture is concentrated
  3. customThe crude product obtained
  4. customafter briefly drying under a high vacuum
  5. customis purified by FC on 6 g of silica gel (eluant Q)

Sources & evidence

ORD record
ord-f20f7da2937440159172eb2bea21145d
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

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