Dimethylformamide → BOC-Lys(CBZ)-Gln-Nle-OMe

HRID 649091Notes

Reaction equation

HRID 649091 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:13][CH2:14][CH3:15])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].FC([C:24]([OH:26])=[O:25])(F)F.[CH2:27]([N:29](CC)CC)C.[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=N[C:38]=2[CH:39]=1.[NH:44]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[C@H:45]([C:51](N[C@H](C(OC)=O)CCCC)=[O:52])[CH2:46][CH2:47][C:48](=O)N.[CH3:70]N(C=O)C>>[NH:44]([C:63]([O:65][C:66]([CH3:67])([CH3:68])[CH3:69])=[O:64])[C@H:45]([C:51]([NH:1][C@H:2]([C:8]([NH:10][C@H:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:13][CH2:14][CH3:15])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:52])[CH2:46][CH2:47][CH2:48][CH2:27][NH:29][C:24]([O:26][CH2:70][C:38]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:39]=1)=[O:25]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 757711-HydroxybenzotriazoleHCID 131715493HCID 131715493, compoundHCID 131715495HCID 131715495, compound

Product 1

HCID 131715496BOC-Lys(CBZ)-Gln-Nle-OMeYield 65%

Procedure

H-Gln-Nle-OMe.TFA salt (XII) (13 mmol) triethylamine (1.76 ml, 13 mmol), HOBT (2.16 g, 16 mmol) and BOC-Lys(CBZ)-ONP (7.6 g, 15 mmol) were dissolved in DMF (30 ml). The reaction mixture was kept basic with small amounts of triethylamine. The mixture was stirred overnight at room temperature, concentrated in vacuo and treated with unsymmetrical dimethylethylenediamine (2 equivs). After 2 hours, EtOAc was added and the product was isolated as described for compound (XI). The solid was washed with petroleum ether (bpt 40°-60° C.) and dried in vacuo over silica gel to give (XIII) (5.5 g; 65%) [αD26 =-16.49° (C=1, DMF) T.l.c. RfA3 0.8.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with unsymmetrical dimethylethylenediamine (2 equivs)
  3. waitAfter 2 hours
  4. additionEtOAc was added
  5. customthe product was isolated
  6. washThe solid was washed with petroleum ether (bpt 40°-60° C.)
  7. customdried in vacuo over silica gel

Sources & evidence

ORD record
ord-d4e73c327d6b441c8accbd6324835e2f
Source dataset
uspto-grants-1988_04
Patent number
US04737487

Reaction notes

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