HCID 13589827, compound → HCID 13589829, compound

HRID 371076Notes

Reaction equation

HRID 371076 reaction equation
C(OC([NH:8][C@H:9]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=[O:20])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:12]([O:11][CH2:10][C@@H:9]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42])[CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=[O:20])[NH2:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 13589827HCID 13589827, compound

Product 1

HCID 13589829HCID 13589829, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

8.00 g (11.5 mmols) of 10-(N-tert-butoxycarbonyl-O-benzyl-L-seryl)-1,5-dibenzyloxycarbonyl-1,5,10-triazadecane was dissolved in 8.0 ml of trifluoroacetic acid, and the solution was stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the residual oil was dissolved in 200 ml of ethyl acetate. The solution was washed with a 5% aqueous solution of sodium hydrogencarbonate and distilled water in this order, and the ethyl acetate layer was dried over anhydrous sodium sulfate. After the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure to obtain 6.82 g (quantitative) of the desired product as an oily substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residual oil was dissolved in 200 ml of ethyl acetate
  3. washThe solution was washed with a 5% aqueous solution of sodium hydrogencarbonate
  4. distillationdistilled water in this order
  5. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. customAfter the desiccant was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-71e2de0416754b83910bc371f7001a03
Source dataset
uspto-grants-1985_07
Patent number
US04529549

Reaction notes

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