(S)-N-((S)-1-(((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide → (4S,7S,10S,13S)-10-Benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 2,6-dimethoxy-4-(prop-2-yn-1-yloxy)benzenesulfonate

HRID 628149Notes

Reaction equation

HRID 628149 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([S:13](Cl)(=[O:15])=[O:14])=[C:7]([O:17][CH3:18])[CH:6]=1)[C:2]#[CH:3].[OH:19][CH2:20][C@:21]([OH:71])([CH3:70])[C:22](=[O:69])[C@@H:23]([NH:28][C:29](=[O:68])[C@@H:30]([NH:38][C:39](=[O:67])[C@@H:40]([NH:45][C:46](=[O:66])[C@@H:47]([NH:56][C:57](=[O:65])[CH2:58][N:59]1[CH2:64][CH2:63][O:62][CH2:61][CH2:60]1)[CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:24][CH:25]([CH3:27])[CH3:26]>>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([O:4][CH2:1][C:2]#[CH:3])[CH:6]=[C:7]([O:17][CH3:18])[C:8]=1[S:13]([O:19][CH2:20][C:21]([OH:71])([CH3:70])[C:22](=[O:69])[C@H:23]([CH2:24][CH:25]([CH3:26])[CH3:27])[NH:28][C:29](=[O:68])[C@H:30]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:38][C:39](=[O:67])[C@H:40]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:45][C:46](=[O:66])[C@H:47]([CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[NH:56][C:57](=[O:65])[CH2:58][N:59]1[CH2:64][CH2:63][O:62][CH2:61][CH2:60]1)(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 86715358(S)-N-((S)-1-(((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamideHCID 867153634-(Propargyloxy)-2,6-dimethoxybenzene-1-sulfonyl chloride

Product 1

HCID 86715362(4S,7S,10S,13S)-10-Benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 2,6-dimethoxy-4-(prop-2-yn-1-yloxy)benzenesulfonate

Procedure

Prepared in a similar manner to compound 13, except from 4-(propargyloxy)-2,6-dimethoxybenzene-1-sulfonyl chloride and (S)—N—((S)-1-(((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide.

Sources & evidence

ORD record
ord-f538bd224c3442bebd6ef70c4045e245
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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