HCID 178513897, compound → HCID 178513939, compound

HRID 1155092Notes

Reaction equation

HRID 1155092 reaction equation
[NH:1]([C:29]([O:31]CC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4]C(=O)N>C(O)(=O)C.[Pd]>[NH:1]1[C:29](=[O:31])[CH2:4][CH2:3][C@H:2]1[C:8]([NH:10][C@H:11]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9]

Participants

4

Reactant 1

HCID 178513897HCID 178513897, compound

Product 1

HCID 178513939HCID 178513939, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.1 g (4 mmoles) of Z-Gln-His-HPro-NH2 are dissolved in 40 ml of acetic acid, 0.4 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is heated to 60°-70° C., maintained at this temperature for 30 minutes, and then evaporated in vacuo. The resulting crude product is subjected to ion exchange and purified as described in Step 5 of Example 15. 618 mg (56%) of Glp-His-HPro-NH2 are obtained; Rf4 =0.08, [α]D25 =-24.0° (c=1%, in methanol). Amino acid analysis: Glu: 0.97 (1.0), His: 1.00 (1.0), HPro: 0.91 (1.0).

Workup

  1. customhydrogen is bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. temperaturethe filtrate is heated to 60°-70° C.
  4. temperaturemaintained at this temperature for 30 minutes
  5. customevaporated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-e3ddfbd801504e79b9e9886317fc94be
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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