Methylamine → HCID 54389452, compound

HRID 2108280Notes

Reaction equation

HRID 2108280 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, 1M 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, 1M 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-e5fdf2f176c4487ea99bb8791b7d28b1
Source dataset
uspto-grants-1990_06
Patent number
US04937243

Reaction notes

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