(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoate → Z-Leu-Asn-Asn-Phe-NHNH-BOC

HRID 1076417Notes

Reaction equation

HRID 1076417 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:26]([NH:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:11][C:12](=[O:14])[NH2:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[CH3:37][CH:38]([CH2:40][C@H:41]([NH:54][C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])[C:42](OC1C=CC([N+]([O-])=O)=CC=1)=[O:43])[CH3:39]>CN(C)C=O>[NH:54]([C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])[C@H:41]([C:42]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:26]([NH:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:11][C:12](=[O:14])[NH2:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:43])[CH2:40][CH:38]([CH3:39])[CH3:37]

Participants

4

Reactant 2

HCID 97647(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoateHCID 131710208HCID 131710208, compound

Product 1

HCID 131710207Z-Leu-Asn-Asn-Phe-NHNH-BOC

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

26.5 g of H-Asn-Asn-Phe-NHNH-BOC are dissolved in 58 ml of warm dimethylformamide, a solution of 24.2 g of Z-Leu-ONP in 16 ml of dimethylformamide is added at room temperature, and the mixture is stirred until it solidifies. After standing overnight the mixture is triturated with ether, filtered off, dissolved in 190 ml of dimethylformamide, and the product reprecipitated by adding dropwise to 1.5 liters of ether. The product is filtered off and washed with ether until free of nitrophenol. Rf = 0.45 in the system chloroform-methanol (7:3) on silica gel.

Workup

  1. customthe mixture is triturated with ether
  2. filtrationfiltered off
  3. dissolutiondissolved in 190 ml of dimethylformamide
  4. customthe product reprecipitated
  5. additionby adding dropwise to 1.5 liters of ether
  6. filtrationThe product is filtered off
  7. washwashed with ether until free of nitrophenol

Sources & evidence

ORD record
ord-d3e61b974c414f3babdc1381937f3585
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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