Hydrogen Peroxide → 1-({(4r,7s,13s,16r)-7-(2-Amino-2-oxoethyl)-13-[(2s)-butan-2-yl]-16-(4-ethoxybenzyl)-10-[(1r)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-l-prolyl-l-ornithylglycinamide

HRID 58309Notes

Reaction equation

HRID 58309 reaction equation
[CH3:1][CH2:2][C@@H:3]([C@@H:5]1[NH:29][C:27](=[O:28])[C@@H:26]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH3:39])=[CH:35][CH:36]=2)[NH:25][C:23](=[O:24])[CH2:22][CH2:21][S:20][S:19][CH2:18][C@@H:17]([C:40]([N:42]2[C@H:46]([C:47]([NH:49][C@H:50]([C:55]([NH:57][CH2:58][C:59]([NH2:61])=[O:60])=[O:56])[CH2:51][CH2:52][CH2:53][NH2:54])=[O:48])[CH2:45][CH2:44][CH2:43]2)=[O:41])[NH:16][C:14](=[O:15])[C@H:13]([CH2:62][C:63]([NH2:65])=[O:64])[NH:12][C:10](=[O:11])[C@H:9]([C@H:66]([OH:68])[CH3:67])[NH:8][C:6]1=[O:7])[CH3:4].O.N.OO>C(#N)C>[CH3:1][CH2:2][C@@H:3]([C@@H:5]1[NH:29][C:27](=[O:28])[C@@H:26]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH3:39])=[CH:35][CH:36]=2)[NH:25][C:23](=[O:24])[CH2:22][CH2:21][S:20][S:19][CH2:18][C@@H:17]([C:40]([N:42]2[C@H:46]([C:47]([NH:49][C@H:50]([C:55]([NH:57][CH2:58][C:59]([NH2:61])=[O:60])=[O:56])[CH2:51][CH2:52][CH2:53][NH2:54])=[O:48])[CH2:45][CH2:44][CH2:43]2)=[O:41])[NH:16][C:14](=[O:15])[C@H:13]([CH2:62][C:63]([NH2:65])=[O:64])[NH:12][C:10](=[O:11])[CH:9]([C@H:66]([OH:68])[CH3:67])[NH:8][C:6]1=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 5311010AtosibanHCID 12896473Azane;hydrate

Product 1

HCID 686131-({(4r,7s,13s,16r)-7-(2-Amino-2-oxoethyl)-13-[(2s)-butan-2-yl]-16-(4-ethoxybenzyl)-10-[(1r)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-l-prolyl-l-ornithylglycinamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.01 g of atosiban acetate is prepared by dissolving the linear atosiban obtained from Example 2 in 250 ml of 10% acetonitrile aqueous solution, adjusting the pH value to 8 to 9 with 30% ammonia water, adding 0.85 g of H2O2, reacting for 30 min at 25° C., monitoring with HPLC (HPLC: 89.5%), filtering after reaction, purifying filtrate by preparative RP-HPLC (column C18 or C8), transferring salt, and freeze-drying, MS: 994.5, HPLC: 99.6%.

Workup

  1. filtrationfiltering
  2. customafter reaction
  3. custompurifying filtrate by preparative RP-HPLC (column C18 or C8)
  4. customfreeze-drying

Sources & evidence

ORD record
ord-99bfbe200c93446d8dacd7e0fc172ea7
Source dataset
uspto-grants-2016_09
Patent number
US09434767B2

Reaction notes

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