Methylamine → HCID 54389452, compound

HRID 1031252Notes

Reaction equation

HRID 1031252 reaction equation
[CH:1]([N:4](C(C)C)CC)(C)C.ClC(OCC)=O.[C:16]([S:19][CH:20]([CH:25]([C:30]([NH:32][C@H:33]([C:43]([NH:45][CH3:46])=[O:44])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)=[O:31])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:21][C:22]([OH:24])=O)(=[O:18])[CH3:17].CN>C1COCC1>[C:16]([S:19][CH:20]([CH2:21][C:22]([NH:4][CH3:1])=[O:24])[CH:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:30]([NH:32][C@H:33]([C:43]([NH:45][CH3:46])=[O:44])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)=[O:31])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 18639816HCID 18639816, compound

Product 1

HCID 54389452HCID 54389452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropylethylamine (0.13 ml, 0.7 mmol) and ethyl chloroformate (0.07 ml, 0.7 mmol) were added to a solution of 3-acetylmercapto-6-methyl-4-[[[1-(S)-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]carbonyl]heptanoic acid (E5, Isomer A; 300 mg, 0.66 mmol) in dry THF (10 ml), at -20° C. After 15 min a solution of methylamine (20 mg) in THF (0.8 ml) was added dropwise and the mixture was stirred in an ice bath for 3 h. The solvent was evaporated in vacuo, and a solution of the residue in dichloromethane was washed successively with water, 1 M hydrochloric acid, water, saturated sodium hydrogen carbonate and brine. The solution was dried (MgSO4) and evaporated in vacuo. Column chromatography on silica (10 g), eluting with 5% methanol/ethyl acetate gave the title compound, mp 195°-199° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washa solution of the residue in dichloromethane was washed successively with water, 1 M hydrochloric acid, water, saturated sodium hydrogen carbonate and brine
  3. dry with materialThe solution was dried (MgSO4)
  4. customevaporated in vacuo
  5. washColumn chromatography on silica (10 g), eluting with 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-2532d14de6784d2d9fc5b8b9ca05f990
Source dataset
uspto-grants-1992_04
Patent number
US05109000

Reaction notes

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