Z-Glu(OtBu)-Val-Val-Glu(OtBu)-Glu(OtBu)-Ala-Glu(OtBu)-Asn-OtBu → H-Glu(OtBu)-Val-Val-Glu(OtBu)-Glu(OtBu)-Ala-Glu(OtBu)-Asn-OtBu

HRID 462871Notes

Reaction equation

HRID 462871 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:52]([NH:54][C@H:55]([C:57]([NH:59][C@H:60]([C:70]([NH:72][C@H:73]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[CH2:74][C:75](=[O:77])[NH2:76])=[O:71])[CH2:61][CH2:62][C:63](=[O:69])[O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:58])[CH3:56])=[O:53])[CH2:43][CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:40])[CH2:30][CH2:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>CN(C=O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:52]([NH:54][C@H:55]([C:57]([NH:59][C@H:60]([C:70]([NH:72][C@H:73]([C:78]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])=[O:79])[CH2:74][C:75](=[O:77])[NH2:76])=[O:71])[CH2:61][CH2:62][C:63](=[O:69])[O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:58])[CH3:56])=[O:53])[CH2:43][CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:40])[CH2:30][CH2:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 1

HCID 13501918Z-Glu(OtBu)-Val-Val-Glu(OtBu)-Glu(OtBu)-Ala-Glu(OtBu)-Asn-OtBu

Product 1

HCID 13501920H-Glu(OtBu)-Val-Val-Glu(OtBu)-Glu(OtBu)-Ala-Glu(OtBu)-Asn-OtBu

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Z-Glu(OtBu)-Val-Val-Glu(OtBu)-Glu(OtBu)-Ala-Glu(OtBu)-Asn-OtBu 42.6 g; 32.0 mmol) in DMF (650 mL) containing 10% Pd-BaSO4 (15.0 g) was hydrogenated in a Vibromixer apparatus for 3 h. The reaction mixture was filtered through a bed of celite which was washed with DMF (5×250 mL). The combined filtrate was evaporated to 600 mL and DMSO (300 mL) added. The resultant solution was used fo the next stage of synthesis. A portion was evaporated to dryness, taken up in MeOH and precipitated with Et2O. The resultant gel was filtered, washed with Et2O and dried in vacuo; mp 246°-249° dec; [α]D25 -18.78° (c 1, DMF); Rf 0.78 (n-BuOH:AcOH:Pyr:H2O; 1-1-1-1). Anal. calc. for C57H99N9O18 (1198.46): C, 57.13; H, 8.33; N, 10.52. Found: C, 56.83; H, 8.32; N, 10.39.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite which
  2. washwas washed with DMF (5×250 mL)
  3. customThe combined filtrate was evaporated to 600 mL and DMSO (300 mL)
  4. additionadded
  5. customthe next stage of synthesis
  6. customA portion was evaporated to dryness
  7. customprecipitated with Et2O
  8. filtrationThe resultant gel was filtered
  9. washwashed with Et2O
  10. customdried in vacuo

Sources & evidence

ORD record
ord-59ee134aa0e243b18548e8de5acfe8b6
Source dataset
uspto-grants-1985_05
Patent number
US04517119

Reaction notes

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