Hydrochloric Acid → HCID 131722144, compound

HRID 1695108Notes

Reaction equation

HRID 1695108 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=O.[NH2:19][C@H:20]([C:24]([N:26]([CH3:55])[C@H:27]([C:31]([N:33]1[CH2:54][CH2:53][CH2:52][C@H:34]1[C:35]([N:37]1[CH2:51][CH2:50][CH2:49][C@H:38]1[C:39]([NH:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])=[O:36])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH:21]([CH3:23])[CH3:22].Cl.C(N(CC)CC)C>CN(C=O)C>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([NH:19][C@H:20]([C:24]([N:26]([CH3:55])[C@H:27]([C:31]([N:33]1[CH2:54][CH2:53][CH2:52][C@H:34]1[C:35]([N:37]1[CH2:51][CH2:50][CH2:49][C@H:38]1[C:39]([NH:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40])=[O:36])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateHCID 10951353H-Val-MeVal-Pro-Pro-NHBn

Product 1

HCID 131722144HCID 131722144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3.74 g Z-D-Pro-OH (15 mmol, BACHEM) and 8.25 g H-Val-MeVal-Pro-Pro-NHBn×HCl (15 mmol) were dissolved in 80 ml dry DMF. After cooling to 0° C., 2.4 g DEPCN (2.25 ml, 15 mmol) and 4.2 ml triethylamine (30 mmol) were added. The reaction mixture was stirred at 0° C. for several hours and room temperature overnight, then the DMF was evaporated under reduced pressure. The residue was diluted with ethyl acetate and thoroughly washed with dilute aqueous HCl (pH 2), water, dilute aqueous NaOH (pH 9-10), and water. The organic phase was dried over sodium sulfate and evaporated to dryness to yield 9.2 g of the desired protected pentapeptide.

Workup

  1. customthe DMF was evaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washthoroughly washed with dilute aqueous HCl (pH 2), water, dilute aqueous NaOH (pH 9-10), and water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated to dryness
  6. customto yield 9.2 g of the

Sources & evidence

ORD record
ord-0215917854754521a8a5e7a5e6f3a1a4
Source dataset
uspto-grants-2012_04
Patent number
US08163698B2

Reaction notes

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