m-Chloroperbenzoic acid → Phe-Pro

HRID 638832Notes

Reaction equation

HRID 638832 reaction equation
Cl[C:2]1[CH:7]=CC=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1.C(OC([NH:19][C@@H:20]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:21]([OH:38])/C=C/CCCNC(=O)OCC1C=CC=CC=1)=O)(C)(C)C.C([C@H](NC(=O)OC(C)(C)C)[C@H](O)[C@@H](O)[C@@H]1CCC[NH:57]1)C1C=CC=CC=1.C([C@H](NC(=O)OC(C)(C)C)[C@H](O)[C@H](O)[C@H]1CCCN1)C1C=CC=CC=1>>[NH2:19][C@H:20]([C:21]([N:57]1[CH2:7][CH2:2][CH2:3][C@H:4]1[C:8]([OH:10])=[O:9])=[O:38])[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 57414000Benzyl (4e,6r,7s)-7-[(tert-butoxycarbonyl)amino]-6-hydroxy-8-phenyl-oct-4-enylcarbamateHCID 57414128Tert-butyl (1s,2s,3s)-1-benzyl-2,3-dihydroxy-3-[(2s)-pyrrolidin-2-yl]propylcarbamateHCID 91359276Tert-butyl (1s,2s,3r)-1-benzyl-2,3-dihydroxy-3-[(2r)-pyrrolidin-2-yl]propylcarbamate

Product 1

HCID 7020642Phe-Pro

Procedure

Eventually, using the benzyl 3-((2S,3S)-3-{[(1S,2S)-1-hydroxy-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}oxiran-2-yl)propylcarbamate, recoverable as a by-product from the epoxidation with m-chloroperbenzoic acid of the allylic alcohol (4E,6R,7S)-7-[(tert-butoxycarbonyl)amino]-6-hydroxy-8-phenyl-oct-4-enylcarbamate (8), and following an approach similar to the one already described for the synthesis of tert-butyl (1S,2S,3S)-1-benzyl-2,3-dihydroxy-3-[(2S)-pyrrolidin-2-yl]propylcarbamate (10), tert-butyl (1S,2S,3R)-1-benzyl-2,3-dihydroxy-3-[(2R)-pyrrolidin-2-yl]propylcarbamate can be obtained as a possible fourth diaminodiol (S,S,R,R) Phe-Pro isostere.

Sources & evidence

ORD record
ord-89909a37c1614b1facd5512d160c3400
Source dataset
uspto-grants-2010_04
Patent number
US07691818B2

Reaction notes

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