4-Methylmorpholine → HCID 12050656, compound

HRID 1276160Notes

Reaction equation

HRID 1276160 reaction equation
CN1CCOCC1.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([OH:25])=O.O.OC1C2N=NNC=2C=CC=1.Cl.[CH2:38]([O:45][C:46]([NH:48][CH2:49][CH2:50][NH2:51])=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:51][CH2:50][CH2:49][NH:48][C:46](=[O:47])[O:45][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:25]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acidHCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochlorideHCID 178526939HCID 178526939, compound

Product 1

HCID 12050656HCID 12050656, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-methylmorpholine (0.47 ml) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid (352.6 mg) [see Preparation 3], hydroxybenzotriazole hydrate (338.4 mg), N-benzyloxycarbonyl-1,2-diaminoethane hydrochloride (499.5 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (552.7 mg) in dichloromethane (15 ml). The reaction mixture was stirred at room temperature for 18 hours, after which time the mixture was diluted with water and the organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 1:1, changing to 1:9, by volume, hexane:ethyl acetate to afford benzyl N-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]carbamate (550 mg) as an oil.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulphate
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 1:1

Sources & evidence

ORD record
ord-af7f6f6f142c4c588fe4f0965fb0a916
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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