Z-Val-ONp → Bis((Cbz-Val-Phe-psi(CHOH))

HRID 1379397Notes

Reaction equation

HRID 1379397 reaction equation
[N+](C1C=CC(O[C:11](=[O:27])[C@H:12]([CH:24]([CH3:26])[CH3:25])[NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=CC=1)([O-])=O.[NH2:28][C@H:29]([C@H:37]([OH:49])[C@@H:38]([OH:48])[C@@H:39]([NH2:47])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[C:14]([NH:13][C@H:12]([C:11]([NH:28][C@H:29]([C@H:37]([OH:49])[C@@H:38]([OH:48])[C@@H:39]([NH:47][C:11](=[O:27])[C@H:12]([CH:24]([CH3:25])[CH3:26])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH:24]([CH3:26])[CH3:25])([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

3

Reactant 2

HCID 112124Z-Val-ONpHCID 10979512(2S,3S,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

Product 1

HCID 452454Bis((Cbz-Val-Phe-psi(CHOH))Yield 5%

Procedure

Cbz-valine p-nitrophenyl ester was coupled to (2S,3S,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane using the procedure of Example 172B to provide the desired compound (Rf 0.42, 5% methanol in chloroform) as a white solid, m.p. 239°-242° C. in 86% yield.

Sources & evidence

ORD record
ord-4aba009b1c4c4b20ae534f8a0dc8ad98
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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