Methanol → HCID 58635457, compound

HRID 855777Notes

Reaction equation

HRID 855777 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:13]([OH:17])[CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21].[CH2:23]([N:30]1[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:37]([N+:44]#[C-:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C[OH:47]>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:13]([OH:17])[CH:14]([CH3:16])[CH3:15])[C:10]([N:22]([CH2:18][CH2:19][CH2:20][CH3:21])[C:33]1([C:45]([NH:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:47])[CH2:34][CH2:35][N:30]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:31][CH2:32]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 887MethanolHCID 8007ButylamineHCID 192201-Benzyl-4-piperidoneHCID 82558Benzyl isocyanideHCID 11184202HCID 11184202, compound

Product 1

HCID 58635457HCID 58635457, compound

Conditions

Temperature
55 °C

Procedure

To a solution of (2R,3R)-2-(t-butoxycarbonylamino)-3-hydroxy-4-methylpentanoic acid (10.5 g) in methanol (340 ml) was added n-butylamine (4.2 ml), N-benzyl-4-piperidone (7.9 ml) and benzylisonitrile (5.2 ml). The reaction mixture was stirred overnight at 55° C. The reaction mixture was concentrated. The obtained residue was purified by column chromatography on silica gel (chloroform:methanol=100:1→75:1→50:1) to give the title compound (19.8 g) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe obtained residue was purified by column chromatography on silica gel (chloroform:methanol=100:1→75:1→50:1)

Sources & evidence

ORD record
ord-4a01bfb73f854adbb67b970996611946
Source dataset
uspto-grants-2007_08
Patent number
US07262193B2

Reaction notes

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