2-(Boc-valinyl-amino)-4-(Cbz-valinyl-amino)-1,5-diphenyl-3-hydroxypentane → 4-(Cbz-valinyl-amino)-2-(valinyl-amino)-1,5-diphenyl-3-hydroxypentane

HRID 847642Notes

Reaction equation

HRID 847642 reaction equation
C([NH:8][C@H:9]([C:13]([NH:15][CH:16]([CH:24]([OH:51])[CH:25]([NH:33][C:34](=[O:50])[C@H:35]([CH:47]([CH3:49])[CH3:48])[NH:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[CH:10]([CH3:12])[CH3:11])(OC(C)(C)C)=O>C(Cl)(Cl)Cl>[C:37]([NH:36][C@H:35]([C:34]([NH:33][CH:25]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:24]([OH:51])[CH:16]([NH:15][C:13](=[O:14])[C@H:9]([CH:10]([CH3:12])[CH3:11])[NH2:8])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:50])[CH:47]([CH3:49])[CH3:48])([O:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:38]

Participants

3

Reactant 1

HCID 228455912-(Boc-valinyl-amino)-4-(Cbz-valinyl-amino)-1,5-diphenyl-3-hydroxypentane

Product 1

HCID 228456514-(Cbz-valinyl-amino)-2-(valinyl-amino)-1,5-diphenyl-3-hydroxypentaneYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 12 with the resultant compound of Example 239 provided a crude hydrochloride salt which was partitioned between chloroform and aqueous NaHCO3, dried over Na2SO4, and concentrated. Chromatography of the residue on silica gel using 3% methanol in chloroform provided in 89% yield the desired compound (Rf 0.5, 10% methanol in chloroform) as a white solid, m.p. 126°-127° C. Mass spectrum: (M+H)+ =603.

Workup

  1. customprovided a crude hydrochloride salt which
  2. customwas partitioned between chloroform and aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a922fe9bd09e4582b5c98b5378bbb3c4
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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