Z-Asn-onp → Z-Asn-Asn-Phe-NH-NH-BOC

HRID 1076416Notes

Reaction equation

HRID 1076416 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[CH:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:36][C:37]([NH:39][C@H:40]([C:45](OC2C=CC([N+]([O-])=O)=CC=2)=[O:46])[CH2:41][C:42]([NH2:44])=[O:43])=[O:38])=[CH:31][CH:30]=1>CN(C)C=O>[NH:39]([C:37]([O:36][CH2:35][C:32]1[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=1)=[O:38])[C@H:40]([C:45]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:46])[CH2:41][C:42](=[O:43])[NH2:44]

Participants

4

Reactant 2

HCID 7021351Z-Asn-onpHCID 131710205H-Asn-Phe-NH-NH-BOC

Product 1

HCID 131710206Z-Asn-Asn-Phe-NH-NH-BOC

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

20.93 g of H-Asn-Phe-NH-NH-BOC are dissolved in 45 ml of dimethylformamide with warming, mixed with 22.7 g of Z-Asn-ONP at room temperature, and stirred until the mixture solidifies. After standing overnight, the solid mass is dissolved in 160 ml of dimethylformamide with warming, precipitated by adding dropwise to 1 liter of ether, and the product is filtered off and washed with acetone until free of nitrophenol. Rf = 0.24 in chloroform-methanol (8:2).

Workup

  1. temperaturewith warming
  2. temperaturewith warming
  3. customprecipitated
  4. additionby adding dropwise to 1 liter of ether
  5. filtrationthe product is filtered off
  6. washwashed with acetone until free of nitrophenol

Sources & evidence

ORD record
ord-97ea28c9299340bba3f8b7fc062110ec
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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