Ethylmorpholine → (S)-4-[6-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-piperazine-1-carboxylic acid cyclobutyl ester

HRID 1970610Notes

Reaction equation

HRID 1970610 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:17][C:18]([O:20][CH2:21][CH:22]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:35]1([O:39][C:40]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[O:41])[CH2:38][CH2:37][CH2:36]1.C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C.C(OCC)(=O)C>[CH:35]1([O:39][C:40]([N:42]2[CH2:47][CH2:46][N:45]([C:14](=[O:15])[C@@H:13]([NH:17][C:18]([O:20][CH2:21][CH:22]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29]4[C:34]3=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:44][CH2:43]2)=[O:41])[CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 51340560Fmoc-L-Nle(6-OBzl)-OHHCID 668544701-Cyclobutoxycarbonylpiperazine

Product 1

HCID 66854519(S)-4-[6-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-piperazine-1-carboxylic acid cyclobutyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 500 mg (S)-6-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid in 7 ml DMF were added at 0° C. 172 mg piperazine-1-carboxylic acid cyclobutyl ester, 0.14 ml N-ethylmorpholine and 357 mg TOTU. After stirring for 3 h the solution was diluted with ethyl acetate and subsequently washed with aqueous LiCl (4%) and half-saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was used without further purification. Yield: 726 mg.

Workup

  1. washsubsequently washed with aqueous LiCl (4%) and half-saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-cb18b4f202c04d428170b84a19129df6
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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