Acetic Acid → HCID 54428006, compound

HRID 614693Notes

Reaction equation

HRID 614693 reaction equation
[CH3:1][O:2][C:3](=[O:44])[C@H:4]([CH2:38][O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[NH:5][C:6](=[O:37])[C@H:7]([C@@H:30]([CH3:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[NH:8][C:9](=[O:29])[C@H:10]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:11][C:12](OCC1C=CC=CC=1)=[O:13].[C:45]([OH:48])(=O)[CH3:46].[CH2:49]([OH:51])[CH3:50].[CH3:52][N:53]([CH:55]=[O:56])C>CO.[Pd]>[CH3:1][O:2][C:3](=[O:44])[C@H:4]([CH2:38][O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[NH:5][C:6](=[O:37])[C@H:7]([C@@H:30]([CH3:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])[NH:8][C:9](=[O:29])[C@H:10]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH:11][C:12](=[O:13])[C@H:52]([C@@H:45]([CH3:46])[O:48][C:32]([CH3:35])([CH3:34])[CH3:33])[NH:53][C:55]([O:51][CH2:49][C:50]1[CH:24]=[CH:23][CH:22]=[CH:10][CH:9]=1)=[O:56]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6228DimethylformamideHCID 53691221HCID 53691221, compound2×

Product 1

HCID 54428006HCID 54428006, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the protected tripeptide of Example 2 (11.2 g., 0.018 mole) in methanol (250 ml.) containing 5% Pd on BaSO4 (6.75 g.) and 1 ml. of glacial acetic acid was hydrogenated as described above for the preparation of the product of Example 2 and evaporated to dryness. The resultant oil was taken up in DMF (70 ml.), cooled to 0° and coupled with N-benzyloxycarbonyl-O-t-butyl-L-threonine N-hydroxysuccinimide ester (7.32 g., 0.018 mole). Workup as described for Example 1 was followed by chromatography on Sephadex LH 20 using 95% ethanol as eluant. Crystallization from ether-gexane gave 12.9 g. (9.8%) of white amorphous product; m.p. 113.5°-115°; [α]D25 + 23.63° (C, 1 DMF); Rf 0.75 (B). Anal. calcd for C41H62N4O10 : C, 63.87; H, 8.11; N, 7.27. Found: C, 63.99; H, 8.18; N, 7.21.

Workup

  1. customevaporated to dryness
  2. temperaturecooled to 0°
  3. customCrystallization from ether-gexane
  4. customgave 12.9 g

Sources & evidence

ORD record
ord-ffbb44d8f98a4ea797e032c7e8f55aa1
Source dataset
uspto-grants-1979_03
Patent number
US04145337

Reaction notes

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