4-Methylmorpholine → Boc-Lys(Z)-Gly-Asp(OBzl)-Val-OBzl

HRID 1376685Notes

Reaction equation

HRID 1376685 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:18]([NH:20][C@H:21]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])[CH2:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4].[CH3:35][C:36]([O:39][C:40]([NH:42][C@H:43]([C:59](ON1C(=O)CCC1=O)=[O:60])[CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[O:41])([CH3:38])[CH3:37].CN1CCOCC1>CN(C=O)C>[NH:42]([C:40]([O:39][C:36]([CH3:38])([CH3:37])[CH3:35])=[O:41])[C@H:43]([C:59]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:18]([NH:20][C@H:21]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])[CH2:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4])=[O:60])[CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:50]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 12686578Boc-Lys(Z)-OSuHCID 131720165H-Gly-Asp(OBzl)-Val-OBzl

Product 1

HCID 131720164Boc-Lys(Z)-Gly-Asp(OBzl)-Val-OBzlYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 583 mg of H-Gly-Asp(OBzl)-Val-OBzl (Example 15Bb) and 477.5 mg of Boc-Lys(Z)-O Su in 10 ml of DMF is adjusted to pH 8.5 with N-methylmorpholine. After stirring for 18 hours the mixture is concentrated and the residue is partitioned between ethyl acetate and water. The organic phase is washed with saturated NaHCO3 solution, 5% KHSO4 /10% K2SO4 solution and saturated NaCl solution, dried and filtered. The filtrate is concentrated and the residue is crystallized from ether. There are obtained 385 mg of Boc-Lys(Z)-Gly-Asp(OBzl)-Val-OBzl, m.p. 95°-101° C.

Workup

  1. concentrationis concentrated
  2. customthe residue is partitioned between ethyl acetate and water
  3. washThe organic phase is washed with saturated NaHCO3 solution, 5% KHSO4 /10% K2SO4 solution and saturated NaCl solution
  4. customdried
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-943c4043fa79456399af06b197b8fdfc
Source dataset
uspto-grants-1997_09
Patent number
US05663297

Reaction notes

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