N-Carbobenzoxy-L-valine → ((R)-3-{(S)-2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyrylamino]-3-methyl-butyrylamino}-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester

HRID 72170

Reaktionsgleichung

Reaktionsgleichung von HRID 72170
[CH2:1]([O:8][P:9]([CH2:18][C@H:19]([OH:43])[CH2:20][NH:21][C:22](=[O:42])[C@@H:23]([NH:27][C:28](=[O:41])[C@@H:29]([NH:33]C(OC(C)(C)C)=O)[CH:30]([CH3:32])[CH3:31])[CH:24]([CH3:26])[CH3:25])([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:44]([NH:54][C@H:55]([C:59]([OH:61])=O)[CH:56]([CH3:58])[CH3:57])([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45]>>[CH2:1]([O:8][P:9]([CH2:18][C@H:19]([OH:43])[CH2:20][NH:21][C:22](=[O:42])[C@@H:23]([NH:27][C:28](=[O:41])[C@@H:29]([NH:33][C:59](=[O:61])[C@@H:55]([NH:54][C:44]([O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:45])[CH:56]([CH3:57])[CH3:58])[CH:30]([CH3:31])[CH3:32])[CH:24]([CH3:25])[CH3:26])([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 726987N-Carbobenzoxy-L-valineHCID 68620254{(R)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyrylamino]-2-hydroxy-propyl}-cyclohexylmethyl-phosphinic acid benzyl ester

Produkt 1

HCID 68621798((R)-3-{(S)-2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyrylamino]-3-methyl-butyrylamino}-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid benzyl ester

Versuchsvorschrift

The resulting product from Step 1 was deprotected in a similar manner as Example 1, step 3, and the compound was used immediately and coupled to N-Cbz-L-valine in accordance with the procedures set forth in Example 12, Method B. The crude product was purified by gradient flash chromatography (methanol/methylene chloride) on a RediSep disposable column. 1H NMR (CD3Cl, 300 MHz): δ 7.45-7.25 (m, 10H), 6.0-5.85 (m, 1H), 5.18-4.92 (m, 4H), 4.50-4.33 (m, 2H), 4.31-4.04 (m, 2H), 3.43-3.26 (m, 2H), 2.25-2.03 (m, 3H), 2.02-1.70 (m, 8H), 1.37-1.10 (m, 4H), 1.04-0.82 (m, 20H). LCMS m/z: [M+H]+=757.9.

Aufarbeitung

  1. customThe crude product was purified by gradient flash chromatography (methanol/methylene chloride) on a RediSep disposable column

Quellen und Nachweise

ORD-Eintrag
ord-66d0a3bbbf7847b5886cbbd27d02ae96
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828974B2

Verknüpfte Notizen

Wird geladen…