Dicyclohexylcarbodiimide → 5-(N-(9-fluorenylmethoxycarbonyl)valylamino)-1,3,4-thiadiazole-2-thione

HRID 1489307Notes

Reaction equation

HRID 1489307 reaction equation
[C:1]([NH:18][C@H:19]([C:23]([OH:25])=O)[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:51][C:52]1[S:56][C:55](=[S:57])[NH:54][N:53]=1>>[CH:7]1[C:6]2[CH:5]([CH2:4][O:3][C:1]([NH:18][C@H:19]([C:23]([NH:51][C:52]3[S:56][C:55](=[S:57])[NH:54][N:53]=3)=[O:25])[CH:20]([CH3:22])[CH3:21])=[O:2])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 688217FMOC-L-valineHCID 27238472-Amino-5-mercapto-1,3,4-thiadiazole

Product 1

HCID 228781345-(N-(9-fluorenylmethoxycarbonyl)valylamino)-1,3,4-thiadiazole-2-thione

Procedure

Fmoc-Valine (0.68 grams), 1-hydroxybenzotriazole (0.36 grams), dicyclohexylcarbodiimide (0.42 grams) and 5-amino-1,3,4-thiadiazole-2-thione (0.4 grams) were reacted according to the procedures described in Example 1. The resulting product was recrystallized from ethanol-pentane. M.P. 141°-144° C. NMR spectrum (d6 -DMSO) 14.06 (s, 1H), 12.56 (s,1H), 8.00-7.60;7.5-7.2 (m, 9H; NH+aromatics) 4.4-4.0 (m, 4H) 2.2-2.0 (m, 1H), 0.98 (bs, 6H).

Workup

  1. customThe resulting product was recrystallized from ethanol-pentane

Sources & evidence

ORD record
ord-4904cd000eab4f4caee6c90da1a0a0d6
Source dataset
uspto-grants-1997_10
Patent number
US05677282

Reaction notes

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