Sodium Carbonate → Boc-His(DNP) 1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamide

HRID 1590759Notes

Reaction equation

HRID 1590759 reaction equation
C(Cl)(=O)C(C)(C)C.[NH:8]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:9]([C:28]([OH:30])=[O:29])[CH2:10][C:11]1[N:15]=[CH:14][N:13]([C:16]2[CH:27]=[CH:26][C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:17]=2[N+:18]([O-:20])=[O:19])[CH:12]=1.C(N1CCCCC1)C.[CH:46]1([CH2:52][C@H:53]([NH2:65])[C@@H:54]([OH:64])[CH2:55][CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1.C(N1[C@@H](CC2CCCCC2)C(CCCC2C=CC=CN=2)OC1(C)C)(OC(C)(C)C)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[NH:8]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:9]([C:28]([OH:30])=[O:29])[CH2:10][C:11]1[N:15]=[CH:14][N:13]([C:16]2[CH:27]=[CH:26][C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:17]=2[N+:18]([O-:20])=[O:19])[CH:12]=1.[CH:46]1([CH2:52][C@H:53]([NH-:65])[C@@H:54]([OH:64])[CH2:55][CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

9

Reactant 6

HCID 10340Sodium Carbonate2×HCID 13007N-EthylpiperidineHCID 62493Pivaloyl chlorideHCID 90690L-Histidine, N-[(1,1-dimethylethoxy)carbonyl]-1-(2,4-dinitrophenyl)-HCID 147243883-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5-(3-(2-pyridyl)propyl)oxazolidineHCID 147243901(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamine

Product 1

HCID 131717863Boc-His(DNP) 1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

550 μl of pivaloyl chloride are added dropwise, at -5° C., to 1.9 g of Boc-His(DNP)-OH, 360 μl of pyridine and 620 μl of N-ethylpiperidine in 50 ml of CH2Cl2. After 10 minutes at -5° C., the mixture is stirred at +10° C. for 10 minutes. It is again cooled to -5° C. and then 1.3 g of 1(S)-cyclohexylmethyl-2(S)-hydroxy-5-(2-pyridyl)-pentylamine (prepared from 1.7 g of 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5-(3-(2-pyridyl)propyl)oxazolidine by the process described under b) and subsequent liberation with Na2CO3) in 20 ml of CH2Cl2 are added. After 1 hour at -5° C., the mixture is left to stand at room temperature for 16 hours. 50 ml of saturated Na2CO3 solution are added, and the mixture is extracted 3 times with EA. The combined organic extracts are dried over Na2SO4 and concentrated. Chromatography on silica gel (EA/MeOH 10:1) yields the title compound.

Workup

  1. additionare added
  2. waitAfter 1 hour at -5° C.
  3. waitthe mixture is left
  4. waitto stand at room temperature for 16 hours
  5. extractionthe mixture is extracted 3 times with EA
  6. dry with materialThe combined organic extracts are dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c0dfb0c93a6a43b7a0891fb97891ba37
Source dataset
uspto-grants-1993_04
Patent number
US05204357

Reaction notes

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