Sodium Hydroxide → 2,5-Di-(N-(Cbz-isoleucinyl)amino)-3,4dihydroxy-1,6-diphenylhexane

HRID 1379393

Reaction equation

HRID 1379393 reaction equation
[NH2:1][C@H:2]([C@@H:10]([OH:22])[C@H:11]([OH:21])[C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+](C1C=CC(O[C:33](=[O:50])[C@H:34]([C@H:46]([CH2:48][CH3:49])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=CC=1)([O-])=O.[OH-:51].[Na+]>O1CCCC1>[C:36]([NH:35][C@H:34]([C:33]([NH:1][CH:2]([CH:10]([OH:22])[CH:11]([OH:21])[CH:12]([NH:20][C:33](=[O:50])[C@H:34]([C@H:46]([CH2:48][CH3:49])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:50])[C@H:46]([CH2:48][CH3:49])[CH3:47])([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:51]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2063382N-[(Phenylmethoxy)carbonyl]-L-isoleucine 4-nitrophenyl esterHCID 10990240(2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

Product 1

HCID 228455822,5-Di-(N-(Cbz-isoleucinyl)amino)-3,4dihydroxy-1,6-diphenylhexaneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 10 mg (0.033 mmol) of the resultant compound of Example 171 and 38.6 mg (0.10 mmol) of Cbz-isoleucine p-nitrophenyl ester in 0.2 ml of tetrahydrofuran was stirred at ambient temperature for 21 h. The resulting misture was diluted with 1 ml of tetrahydrofuran, treated with 0.5 ml of 3N NaOH, stirred for 45 min, extracted with chloroform, washed sequentially with 3N NaOH and saturated brine, dried over MgSO4, and concentrated. The residue was purified on silica gel by eluting with 2% methanol in chloroform to provide 23 mg (86%) of the desired compound. Mass spectrum: (M+H)+ =795.

Workup

  1. stirringstirred for 45 min
  2. extractionextracted with chloroform
  3. washwashed sequentially with 3N NaOH and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washby eluting with 2% methanol in chloroform

Sources & evidence

ORD record
ord-bb104e4cf83f4c12817ede28c56b2363
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Linked notes

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