HCID 15931055, compound → HCID 22881979, compound

HRID 502320Notes

Reaction equation

HRID 502320 reaction equation
[NH:1]([C:26]([CH3:28])=[O:27])[C@H:2]([C:11]([NH:13][C@H:14]([C:18]([NH:20][C@H:21]([C:23](O)=[O:24])[CH3:22])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(OC([NH:35][CH:36]([C:45](=[O:56])[CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[Cl:55])[CH2:37][C:38]([O:40]C(C)(C)C)=[O:39])=O)C=C>>[C:26]([NH:1][C@H:2]([C:11]([NH:13][C@H:14]([C:18]([NH:20][C@H:21]([C:23]([CH:37]([C@H:36]([NH2:35])[C:45](=[O:56])[CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[Cl:55])[C:38]([OH:40])=[O:39])=[O:24])[CH3:22])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)(=[O:27])[CH3:28]

Participants

3

Reactant 2

HCID 15931055HCID 15931055, compoundHCID 18465758HCID 18465758, compound

Product 1

HCID 22881979HCID 22881979, compound

Procedure

N-Acetyl-(S)-tyrosinyl-(S)-valinyl-(S)-alaninyl-3(S)-amino-5-(2-chlorobenzyloxy)-4-oxo-pentanoic acid (89) was prepared from Ac-Tyr-Val-Ala-OH and (3S) t-butyl N-(allyloxycarbonyl)-3-amino-5-(2-chlorophenyl-methoxyl)-4-oxo-pentanoate (prepared by a similar method as 82) to give a white solid: 1H NMR (DMSO-d6) δ 9.15 (s, 1H), 8.5 (d, 1H), 7.98 (d, 1H), 7.75 (d, 1H), 7.55-7.3 (m, 4H), 7.0 (d, 1H), 6.6 (d, 2H), 4.6-4.3 (m, 6H), 4.3-4.1 (m, 2H), 2.9 (d, 1H), 2.76 (dd, 1H), 2.7-2.5 (m, 2H), 1.95 (m, 1H), 1.75 (s, 3H), 1.2 (d, 3H), 0.9-0.7 (dd, 6H)

Workup

  1. customprepared by a similar method as 82)
  2. customto give a white solid

Sources & evidence

ORD record
ord-8dd4bc71ba134a96ac6a4a630ea81d9b
Source dataset
uspto-grants-2010_08
Patent number
US07772366B2

Reaction notes

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