HCID 178473176, compound → HCID 178484300, compound

HRID 1196457Notes

Reaction equation

HRID 1196457 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:27]([NH:29][C@@H:30]([CH2:41][CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[C@@H:31]([OH:40])[CH2:32][S:33][CH2:34][C:35]([O:37]CC)=O)=[O:28])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CN(C)CCN>[C:1]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:27]([NH:29][C@@H:30]([CH2:41][CH:42]1[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]1)[C@@H:31]([OH:40])[CH2:32][S:33][CH2:34][C:35]([N:8]([CH3:1])[CH2:9][CH2:17][NH:19][CH3:20])=[O:37])=[O:28])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

3

Reactant 1

HCID 178473176HCID 178473176, compound

Product 1

HCID 178484300HCID 178484300, compound

Reagents, catalysts & solvents 1

HCID 66053N,N-DimethylethylenediamineSolvent

Procedure

To 74 mg (0.11 mmole) of ethyl 2-[[(2R,3S)-3-(Boc-L-phenylalanyl-L-histidylamino)-4-cyclohexyl-2-hydroxy-1-butyl]thio]acetate was added 100 μl of N,N-dimethylethylenediamine. The mixture, which was stirred at room temperature in a stoppered flask, became homogeneous within a few minutes. After 18 hours, the mixture, which had gelled, was triturated thoroughly with hot ether. The resulting solid was collected on a filter and washed several times with ether, triturating thoroughly each time. This yielded 68 mg (86%) of white powder, mp 160°-164° (preliminary softening), virtually homogeneous by TLC (90:10:1 CHCl3 --MeOH-cond. NH4OH). Mass spectrum and 200 MHz NMR (DMSO d6) were in accord with the assigned structure.

Workup

  1. waitbecame homogeneous within a few minutes
  2. customwas triturated thoroughly with hot ether
  3. customThe resulting solid was collected on
  4. filtrationa filter
  5. washwashed several times with ether
  6. customtriturating thoroughly each time

Sources & evidence

ORD record
ord-5b6a8e98a40840d0adb55161c72a8258
Source dataset
uspto-grants-1992_05
Patent number
US05114925

Reaction notes

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