4-Methylmorpholine → N-[N2-[(1,1-dimethylethoxy) carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysinyl]-L-alanine 1,1-dimethylethyl ester

HRID 34492

Reaction equation

HRID 34492 reaction equation
CN1CCOCC1.[CH3:8][C:9]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])([CH3:11])[CH3:10].N#N.[CH3:20][C:21]([CH3:46])([O:23][C:24]([NH:26][C@H:27]([C:43](O)=[O:44])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:25])[CH3:22].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:8][C:9]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH:15][C:43](=[O:44])[C@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])[NH:26][C:24]([O:23][C:21]([CH3:46])([CH3:20])[CH3:22])=[O:25])([CH3:11])[CH3:10]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 89016L-Alanine 1,1-dimethylethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

Product 1

HCID 53963310N-[N2-[(1,1-dimethylethoxy) carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysinyl]-L-alanine 1,1-dimethylethyl esterYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methylmorpholine (3.3 ml) was added to a suspension of L-alanine 1,1 -dimethylethyl ester (4.0 g), N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (11.4 g), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (5.8 g) and 1-hydroxybenzotriazole (4.1 g) in dichloromethane (150 ml). The resulting mixture was allowed to stand for 18 hours, and was then poured into distilled water (200 ml). The organic phase was separated, washed with water, saturated sodium hydrogen carbonate, dilute aqueous citric acid, brine and dried over anhydrous magnesium sulphate. The solvent was removed under reduced pressure to yield N-[N2 -[(1,1-dimethylethoxy) carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysinyl]-L-alanine 1,1-dimethylethyl ester (12.6 g) as a foam.

Workup

  1. additionwas then poured
  2. distillationinto distilled water (200 ml)
  3. customThe organic phase was separated
  4. washwashed with water, saturated sodium hydrogen carbonate, dilute aqueous citric acid, brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-24498aec61e446009080dc62880529ac
Source dataset
uspto-grants-1988_08
Patent number
US04761483

Linked notes

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