Methanol → HCID 58635457, compound

HRID 1181583Notes

Reaction equation

HRID 1181583 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-d808ccd1bc164124a8a5a3e8380c1a90
Source dataset
uspto-grants-2007_10
Patent number
US07285552B2

Reaction notes

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