1-Hydroxybenzotriazole → HCID 69756876, compound

HRID 1765687Notes

Reaction equation

HRID 1765687 reaction equation
[CH3:1][CH:2]([CH3:36])[CH2:3][S:4]([CH2:7][CH:8]([NH:27][C:28]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])[C:9](=[O:26])[NH:10][CH:11]([C:14]([C:16]1[O:20][N:19]=[C:18](C2SC=CC=2)[N:17]=1)=[O:15])[CH2:12][CH3:13])(=[O:6])=[O:5].C1C=CC2N(O)N=NC=2C=1.N[C@@H](CC)C(C1ON=[C:53]([C:56](C)([CH3:58])[CH3:57])N=1)O>ClCCl>[C:56]([C:18]1[N:17]=[C:16]([CH:14]([OH:15])[CH:11]([NH:10][C:9]([CH:8]([NH:27][C:28]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)=[O:29])[CH2:7][S:4]([CH2:3][CH:2]([CH3:36])[CH3:1])(=[O:5])=[O:6])=[O:26])[CH2:12][CH3:13])[O:20][N:19]=1)([CH3:58])([CH3:57])[CH3:53]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 10289588HCID 10289588, compoundHCID 60054525HCID 60054525, compound

Product 1

HCID 69756876HCID 69756876, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Cyclohexylcarbodiimide-N′-methylpolystyrene (0.526 g, 1 mmol, loading 1:9 mol/g) was suspended in dichloromethane (20 mL). 3-(2-methyl-propane-1-sulfonyl)-2-[(morpholine-4-carbonyl)-amino]-propionic acid (0.242 g, 0.6 mmol, reference Example 5) and HOBt (0.114 g, 0.85 mmol) were added and the reaction mixture was stirred for 20 minutes. (2S)-2-Amino-1-(3-tert-butyl-[1,2,4]oxadiazol-5-yl)-butan-1-ol (0.107 g, 0.5 mmol, Reference Example 6) was added and stirring continued for 5 hours. Silicycle Triamine (1.27 g, 5 mmol) was added and the mixture stirred for 15 hours. The reaction mixture was filtered under suction and the filtrate concentrated to give morpholine-4-carboxylic acid [1-{1-[(3-tert-butyl-1,2,4-oxadiazol-5-yl)-hydroxy-methyl]-propylcarbamoyl}-2-(2-methyl-propane-1-sulfonyl)-ethyl]-amide (0.271 g), [LC/MS m/z=518 (M+H+)].

Workup

  1. stirringstirring
  2. waitcontinued for 5 hours
  3. stirringthe mixture stirred for 15 hours
  4. filtrationThe reaction mixture was filtered under suction
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-beca41f9f1b94fba95c4ce8ecdb277c4
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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