Benzenepropanoic acid → (S)-3-Methyl-N-[(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]-2-[(S)-2-(3-phenyl-propionyl-amino)-3-(2,3,4-trimethoxy-phenyl)-propionylamino]-butyramide

HRID 1920627Notes

Reaction equation

HRID 1920627 reaction equation
C(O[C:6](=[O:33])[NH:7][C@H:8]([C:12](=[O:32])[NH:13][C@H:14]([B:19]1[O:27][C@H:26]2[C@:21]([CH3:31])([C@H:22]3[CH2:28][C@@H:24]([CH2:25]2)[C:23]3([CH3:30])[CH3:29])[O:20]1)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(O[C:39]([NH:41][C@@H:42]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[C:48]=1[O:57][CH3:58])C(O)=O)=[O:40])(C)(C)C.[C:59]1([CH2:65][CH2:66]C(O)=O)[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>>[CH3:11][CH:9]([CH3:10])[C@H:8]([NH:7][C:6](=[O:33])[C@@H:42]([NH:41][C:39](=[O:40])[CH2:66][CH2:65][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([O:55][CH3:56])[C:48]=1[O:57][CH3:58])[C:12]([NH:13][C@H:14]([B:19]1[O:27][C@H:26]2[C@:21]([CH3:31])([C@H:22]3[CH2:28][C@@H:24]([CH2:25]2)[C:23]3([CH3:29])[CH3:30])[O:20]1)[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:32]

Participants

4

Reactant 3

HCID 107Benzenepropanoic acidHCID 60024443(S)-2-Tert-butoxycarbonylamino-3-(2,3,4-trimethoxy-phenyl)-propionic acidHCID 67492646{(S)-2-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-]propyl}-carbamic acid tert-butyl ester

Product 1

HCID 20823725(S)-3-Methyl-N-[(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]-2-[(S)-2-(3-phenyl-propionyl-amino)-3-(2,3,4-trimethoxy-phenyl)-propionylamino]-butyramide

Procedure

The title compound is prepared from {(S)-2-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]-propyl}-carbamic acid tert-butyl ester by reiteration of the 2-step (deprotection/coupling) procedure described in example 1 but using (S)-2-(tert-butyloxycarbonyl-amino)-3-(2,3,4-trimethoxy-phenyl)-propionic acid and 3-Phenyl-propionic acid (Fluka, Buchs, Switzerland) 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-f5ab2a2d1b8d4dbca6276543d64c36a8
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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