Benzenepropanoic acid → (S)-N-{(S)-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]-ethyl}-2-(3-phenyl-propionylamino)-3-(2,3,4-trimethoxy-phenyl)-propionamide

HRID 1920646Notes

Reaction equation

HRID 1920646 reaction equation
C(O[C:6](=[O:31])[NH:7][C@H:8]([C:10](=[O:30])[NH:11][C@H:12]([B:17]1[O:25][C@H:24]2[C@:19]([CH3:29])([C@H:20]3[CH2:26][C@@H:22]([CH2:23]2)[C:21]3([CH3:28])[CH3:27])[O:18]1)[CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:9])(C)(C)C.[NH2:32][C@@H:33]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([O:46][CH3:47])[C:39]=1[O:48][CH3:49])C(O)=O.[C:50]1([CH2:56][CH2:57][C:58](O)=[O:59])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH3:16][CH:14]([CH3:15])[CH2:13][C@H:12]([NH:11][C:10]([C@@H:8]([NH:7][C:6](=[O:31])[C@@H:33]([NH:32][C:58](=[O:59])[CH2:57][CH2:56][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([O:46][CH3:47])[C:39]=1[O:48][CH3:49])[CH3:9])=[O:30])[B:17]1[O:25][C@H:24]2[C@:19]([CH3:29])([C@H:20]3[CH2:26][C@@H:22]([CH2:23]2)[C:21]3([CH3:28])[CH3:27])[O:18]1

Participants

4

Reactant 3

HCID 107Benzenepropanoic acidHCID 28182480(S)-2-Amino-3-(2,3,4-trimethoxy-phenyl)-propionic acidHCID 67492721{(S)-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]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 20823727(S)-N-{(S)-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]-ethyl}-2-(3-phenyl-propionylamino)-3-(2,3,4-trimethoxy-phenyl)-propionamide

Procedure

The title compound is prepared from {(S)-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]-ethyl}-carbamic acid tert-butyl ester by reiteration of the 2-step (deprotection/coupling) procedure described in example 1 but using (S)-2-Amino-3-(2,3,4-trimethoxy-phenyl)-propionic acid and 3-Phenyl-propionic acid (Fluka) as the partners in each coupling reaction (step B, example 1), respectively.

Workup

  1. customin each coupling reaction (step B, example 1)

Sources & evidence

ORD record
ord-155c25ce4dfd41e691166aec646e9924
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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