1-Hydroxybenzotriazole → HCID 18682345, compound

HRID 381517Notes

Reaction equation

HRID 381517 reaction equation
[CH3:1][CH:2]([CH3:29])[CH2:3][CH:4]([NH:8][C:9](=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])=[O:19])=[CH:13][CH:12]=1)[C:5](O)=[O:6].Cl.[CH2:31]([O:38][C:39](=[O:45])[CH2:40][CH:41]([OH:44])[CH2:42][NH2:43])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(N(CC)CC)C>[CH2:31]([O:38][C:39](=[O:45])[CH2:40][CH:41]([OH:44])[CH2:42][NH:43][C:5](=[O:6])[CH:4]([NH:8][C:9](=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])=[O:19])=[CH:13][CH:12]=1)[CH2:3][CH:2]([CH3:29])[CH3:1])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18313824HCID 18313824, compoundHCID 69693133HCID 69693133, compound

Product 1

HCID 18682345HCID 18682345, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-methyl-2-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-pentanoic acid (3.6 g), 4-amino-3-hydroxy-butyric acid benzyl ester hydrochloride (1.6 g), triethylamine (1 ml) and HOBT (1.06 g) in DMF (50 ml) at room temperature was added EDCl (1.63 g). After stirring 16 h the mixture was poured into 1500 ml ice-water and stirred for 20 min. The resulting ppt was filtered and dried to give a creme colored solid. Recrystallization from EtOAc gave 2.1 g of the title compound as a white solid. MS [M+1]+ 589.2; 1H nmr (400 MHz, DMSO-d6) δ0.73-0.81 (m, 6H), 1.37-1.49 (m, 3H), 2.19 (s, 3H), 2.20-2.28 (m, 1H), 2.46-2.49 (m, 1H), 2.99-3.09 (m, 2H), 3.33 (q, J=13.8 Hz, 2H), 3.90 (m, 1H), 4.19-4.23 (m, 1H), 5.05 (m , 2H), 6.88 (t, 1H), 7.06-7.12 (m, 4H), 7.26-7.34 (m, 6H), 7.75 (d, J=8.1 Hz, 1H), 7.92 (dt, 1H), 8.06 (s, 1H), 8.10 (d, J=8.1 Hz, 1H), 9.13 (s, 1H).

Workup

  1. stirringstirred for 20 min
  2. filtrationThe resulting ppt was filtered
  3. customdried
  4. customto give a creme colored solid
  5. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-a04463ffc99a4e0b86d85467eac89f4b
Source dataset
uspto-grants-2001_10
Patent number
US06306887B1

Reaction notes

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