3-Phenoxyphenylacetic acid → (S)-2-{(S)-3-(3,4-Dimethoxy-phenyl)-2-[2-(3-phenoxy-phenyl)-acetylamino]-propionylamino}-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]-butyramide

HRID 585887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585887
C(OC(=O)[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.CC(O[C:39]([NH:41][C@H:42]([C:54]([OH:56])=O)[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([O:52][CH3:53])[CH:45]=1)=[O:40])(C)C.[O:57]([C:64]1[CH:65]=[C:66]([CH2:70]C(O)=O)[CH:67]=[CH:68][CH:69]=1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>>[CH3:53][O:52][C:46]1[CH:45]=[C:44]([CH2:43][C@H:42]([NH:41][C:39](=[O:40])[CH2:70][C:66]2[CH:67]=[CH:68][CH:69]=[C:64]([O:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH:65]=2)[C:54]([NH:7][C@@H:8]([CH:9]([CH3:11])[CH3:10])[C:12]([NH:13][C@H:14]([B:19]2[O:27][C@H:26]3[C@:21]([CH3:31])([C@H:22]4[CH2:28][C@@H:24]([CH2:25]3)[C:23]4([CH3:30])[CH3:29])[O:20]2)[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:32])=[O:56])[CH:49]=[CH:48][C:47]=1[O:50][CH3:51]

Komponenten

4

Edukt 3

HCID 1417493-Phenoxyphenylacetic acidHCID 10829890N-((1,1-Dimethylethoxy)carbonyl)-3-methoxy-O-methyl-L-tyrosineHCID 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

Produkt 1

HCID 10169507(S)-2-{(S)-3-(3,4-Dimethoxy-phenyl)-2-[2-(3-phenoxy-phenyl)-acetylamino]-propionylamino}-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]-butyramide

Versuchsvorschrift

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 Boc-L-3,4-dimethoxyphenylalanine (Synthetech) and (3-Phenoxyphenyl)-acetic acid (Trans World Chemicals, Inc.; Rockville, Md., USA) as the partners in each coupling reaction (step B, example 1), respectively. The title compound is obtained as a foam; ES-MS: 782.3 [M+H]+; HPLC: single peak at tR=11.76 min (System 1); Rf=0.61 (CH2Cl2/MeOH, 90/10).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-317b7f27b4ec4cb7b2415333eaf97436
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933290B2

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