Diisopropylcarbodiimide → HCID 67399332, compound

HRID 914511Notes

Reaction equation

HRID 914511 reaction equation
[C:1]([CH2:4][C:5]1[N:6]=[C:7]([S:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[S:8][CH:9]=1)([OH:3])=O.[CH2:17]([O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)[CH3:18].C1C=C2N=NN(O)C2=CC=1.O.C(N=C=NC(C)C)(C)C>CN(C)C=O>[CH2:17]([O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:1](=[O:3])[CH2:4][C:5]2[N:6]=[C:7]([S:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[S:8][CH:9]=2)=[CH:26][CH:27]=1)[CH3:18]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 225219p-Aminophenylacetic acid ethyl ester2×HCID 27960291-Hydroxybenzotriazole hydrateHCID 67399201HCID 67399201, compound

Product 1

HCID 67399332HCID 67399332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An operation similar to that of Example 461-5 was performed 3 times using 2-{[4-(carboxymethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid resin obtained in Example 461-4 and 4-aminophenylacetic acid ethyl ester. To a suspension of the obtained resin in dimethylformamide (30 mL) were added HOBT monohydrate (0.92 g), diisopropylcarbodiimide (0.93 ml) and 4-aminophenylacetic acid ethyl ester (1.1 g), and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the reaction mixture, washed once each with dimethylformamide and methanol, twice with dimethylformamide, once with methanol, three times with tetrahydrofuran and finally once with methanol, and vacuum dried to give the title pale-brown resin (3.1 g).

Workup

  1. filtrationThe resin was collected by filtration from the reaction mixture
  2. washwashed once each with dimethylformamide and methanol
  3. dry with materialtwice with dimethylformamide, once with methanol, three times with tetrahydrofuran and finally once with methanol, and vacuum dried

Sources & evidence

ORD record
ord-aec8cd0ab72c44d6b6d7286d819de817
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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