(2R)-2-(((tert-butoxy)carbonyl)amino)-4-methanesulfonylbutanoic acid → BOC-(D)-Met(O2)-Gly-Phe-NHNH-COCH3

HRID 1277408Notes

Reaction equation

HRID 1277408 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][NH:17][C:18]([CH3:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH:21]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:22]([C:29](O)=[O:30])[CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26]>>[NH:21]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:22]([C:29]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][NH:17][C:18]([CH3:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4])=[O:30])[CH2:23][CH2:24][S:25]([CH3:28])(=[O:26])=[O:27]

Participants

3

Reactant 2

HCID 12802585(2R)-2-(((tert-butoxy)carbonyl)amino)-4-methanesulfonylbutanoic acidHCID 131712285H-Gly-Phe-NHNH-COCH3

Product 1

HCID 12802564BOC-(D)-Met(O2)-Gly-Phe-NHNH-COCH3Yield 52.7%

Procedure

Using H-Gly-Phe-NHNH-COCH3 (0.69 g) and BOC-(D)-Met(O2)-OH (0.66 g), the desired compound (0.67 g) is obtained in a similar manner to (III)of Example 45. m.p. 198°-199° C.(decomp.), [α]D23 -2.5°(c=0.49, DMF), Rf1 =0.25.

Sources & evidence

ORD record
ord-7fb8955299554cc8bef35aa8019720c5
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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