{(S)-3-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)butylcarbamoyl]-butyl}-carbamic acid tert-butyl ester → (S)-2-[(S)-2-(Biphenyl-3-ylamino)-3-(3,4-dimethoxy-phenyl)-propionylamino]-4-methyl-pentanoic acid [(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butyl]-amide

HRID 1920639Notes

Reaction equation

HRID 1920639 reaction equation
C(O[C:6](=[O:34])[NH:7][C@H:8]([C:13](=[O:33])[NH:14][C@H:15]([B:20]1[O:28][C@H:27]2[C@:22]([CH3:32])([C@H:23]3[CH2:29][C@@H:25]([CH2:26]2)[C:24]3([CH3:31])[CH3:30])[O:21]1)[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.[C:35]1([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:40]=[CH:39][CH:38]=[C:37]([NH:41][C@@H:42]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[CH:48]=2)C(O)=O)[CH:36]=1>>[CH3:18][CH:17]([CH3:19])[CH2:16][C@H:15]([NH:14][C:13](=[O:33])[C@@H:8]([NH:7][C:6](=[O:34])[C@@H:42]([NH:41][C:37]1[CH:36]=[C:35]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:40]=[CH:39][CH:38]=1)[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[CH:48]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])[B:20]1[O:28][C@H:27]2[C@:22]([CH3:32])([C@H:23]3[CH2:29][C@@H:25]([CH2:26]2)[C:24]3([CH3:30])[CH3:31])[O:21]1

Participants

3

Reactant 2

HCID 67492464{(S)-3-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)butylcarbamoyl]-butyl}-carbamic acid tert-butyl esterHCID 67492614(S)-2-(Biphenyl-3-ylamino)-3-(3,4-dimethoxyphenyl)-propionic acid

Product 1

HCID 10123078(S)-2-[(S)-2-(Biphenyl-3-ylamino)-3-(3,4-dimethoxy-phenyl)-propionylamino]-4-methyl-pentanoic acid [(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butyl]-amide

Procedure

The title compound is prepared as described in example 1 but using {(S)-3-Methyl-1-[(R)-3-methyl-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-butylcarbamoyl]-butyl}-carbamic acid tert-butyl ester and (S)-2-(Biphenyl-3-ylamino)-3-(3,4-dimethoxy-phenyl)-propionic acid.

Sources & evidence

ORD record
ord-e2e62b920e284467ad9ed57713397fce
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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