N-carbobenzyloxyalanine → HCID 86608597, compound

HRID 2111539Notes

Reaction equation

HRID 2111539 reaction equation
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@H:2]([C:4](O)=[O:5])[CH3:3].Cl.[C:18]1([CH:24]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@H:25]([NH2:48])[CH:26]=[CH:27][S:28]([CH:31]=[CH:32][C@@H:33]([NH2:47])[CH:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:30])=[O:29])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:49]1([CH:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:25]([NH:48][C:4](=[O:5])[C@H:2]([CH3:3])[NH:1][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH:26]=[CH:27][S:28]([CH:31]=[CH:32][C@@H:33]([NH:47][C:4](=[O:5])[C@H:2]([CH3:3])[NH:1][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)(=[O:30])=[O:29])[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

3

Reactant 2

HCID 736104N-carbobenzyloxyalanineHCID 131727420Phenyl-(3S)-3-amino-4-phenylbut-1-enyl Sulfone Hydrochloride

Product 1

HCID 86608597HCID 86608597, compoundYield 88%

Procedure

Cbz-Ala-Phe-VS-Ph was prepared from Cbz-Ala-OH and Phe-VS-Ph.HCl using standard mixed anhydride coupling method, yield 88%. 1H-NMR (CDCl3) δ 1.25 (d, 3H, Ala-CH3), 2.91 (dq, 2H, CH2-Phe), 4.10 (m, 1H, α-H), 4.80-4.90 (m, 1H, α-H), 5.10 (s, 2H, Cbz), 6.34 (b, 1H, NH), 6.39 (d, 1H, CH═), 6.90-6.98 (dd, 1H, CH═), 7.10-7.39 (m, 10H, 2×Ph), 7.55 (t, 2H, SO2-Ph), 7.65 (t, 1H, SO2-Ph), 7.91 (d, 2H, SO2-Ph). 13C NMR (400 MHz, CDCl3) δ 172.1, 156.3, 144.4, 140.8, 135.7, 134.2, 133.6, 131.2, 129.5, 129.4×3, 129.3, 128.8×2, 128.7, 128.6, 128.4, 128.3, 127.8, 127.3, 126.9, 67.6, 51.7, 51.6, 40.2, 19.4.

Sources & evidence

ORD record
ord-80c3a8b5d1814d2b9b05e5fd0b05cf82
Source dataset
uspto-grants-2009_04
Patent number
US07521427B2

Reaction notes

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