Ethylmorpholine → HCID 67806908, compound

HRID 1609618Notes

Reaction equation

HRID 1609618 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:33]([O:40][C:41]([CH:43]1[CH2:51][CH:50]2[CH:45]([CH2:46][CH2:47][CH2:48][CH2:49]2)[NH:44]1)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:33]([O:40][C:41]([CH:43]1[CH2:51][CH:50]2[CH:45]([CH2:46][CH2:47][CH2:48][CH2:49]2)[N:44]1[C:4](=[O:6])[C@H:2]([CH3:3])[NH:1][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:42])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 19902522Benzyl octahydro-1H-indole-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 67806908HCID 67806908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19 g of Boc-Ala-OH are dissolved in 100 ml of dimethylformamide, and 13 ml of N-ethylmorpholine, 13.5 g of HOBt and 29.6 g of octahydroindole-2-carboxylic acid benzyl ester hydrochloride are added to the solution. The mixture is cooled in an ice bath, 21 g of dicyclohexylcarbodiimide are added to it, and it is stirred for 15 hours at room temperature. The precipitated urea is filtered off under suction, and the filtrate is concentrated in vacuo and taken up in ethyl acetate. The solution is extracted 3 times in each case with aqueous KHSO4 solution, KHCO3 solution and saturated NaCl solution and the organic phase is concentrated in vacuo. Yield: 38.5 g. NMR: 1.26 (d, 3H); 1.40 (s, 9H); 1,1-2,4 (m, 12H); 3.2-3.9 (m, 2H); 5.28 (s, 2H); 7.31 (s, 5H).

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. filtrationThe precipitated urea is filtered off under suction
  3. concentrationthe filtrate is concentrated in vacuo
  4. extractionThe solution is extracted 3 times in each case with aqueous KHSO4 solution, KHCO3 solution and saturated NaCl solution
  5. concentrationthe organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-66c018cfc7264a1d9ae9b5b3a5408218
Source dataset
uspto-grants-1995_03
Patent number
US05401766

Reaction notes

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