Methanol → HCID 136085214, compound

HRID 1893208Notes

Reaction equation

HRID 1893208 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH:10]([C:25]([NH:27]O)=[NH:26])[CH2:11][CH2:12][C@H:13]([O:23][CH3:24])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:30]([C:36]([O:38][CH3:39])=[O:37])#[C:31][C:32](OC)=[O:33].C[OH:41]>>[CH2:16]([O:15][CH2:14][C@@H:13]([O:23][CH3:24])[CH2:12][CH2:11][CH:10]([C:25]1[NH:27][C:32](=[O:33])[C:31]([OH:41])=[C:30]([C:36]([O:38][CH3:39])=[O:37])[N:26]=1)[N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:29])[CH2:8][CH3:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 12980Dimethyl acetylenedicarboxylateHCID 178465443HCID 178465443, compound

Product 1

HCID 136085214HCID 136085214, compound

Procedure

To a solution of tert-butyl{(4S)-5-(benzyloxy)-1-[(hydroxyamino)(imino)methyl]-4-methoxypentyl}ethylcarbamate (72.6 g, 177 mmol) in MeOH (1773 ml) at 0° C. was added dimethyl acetylene dicarboxylate (26.3 mL, 213 mmol). The reaction mixture was stirred at ambient temperature overnight and then concentrated in vacuo. The residue was dissolved in toluene and concentrated in vacuo (3×) to remove MeOH. The crude product was used in the next reaction without purification. LC-MS: 553.5 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in toluene
  3. concentrationconcentrated in vacuo (3×)
  4. customto remove MeOH
  5. customThe crude product was used in the next reaction without purification

Sources & evidence

ORD record
ord-79cfc5525dd74c4c9a6009b466eff8ad
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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