Benzyl isocyanate → N-Benzylaminocarbonyl-L-prolyl-L-proline benzyl ester

HRID 1720500Notes

Reaction equation

HRID 1720500 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:28])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1.[CH2:37]([N:44]=[C:45]=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH2:1]([O:8][C:9](=[O:29])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:28])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:45]([NH:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:46])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 76639Benzyl isocyanateHCID 13091041Boc-prolylproline benzyl esterHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 54203628N-Benzylaminocarbonyl-L-prolyl-L-proline benzyl ester

Procedure

N-(t-Butoxycarbonyl)-L-prolyl-L-proline benzyl ester (3.60 g) was treated with 4N hydrochloric acid/1,4-dioxane and then reacted with benzylisocyanate (1.2 ml) as in Example 21-B) to give 2.98 g of the title compound as crystals.

Sources & evidence

ORD record
ord-b84af5812abb4f50ab18d772935500d3
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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