Isobutyric anhydride → Isobutyrylproline

HRID 1274062Notes

Reaction equation

CC[C@@H]([C@H]1NC(=O)[C@@H](NC([C@H](N(C([C@H]2N(C(C(O)C)=O)CCC2)=O)C)CC(C)C)=O)[C@@H](C)OC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H]2N(CCC2)C(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)C(=O)[C@H:11]([CH:76]([CH3:78])[CH3:77])[O:10]C(=O)C[C@@H]1O)C.[NH:80]1[CH2:87][CH2:86][CH2:85][C@H:81]1[C:82]([OH:84])=[O:83].C(OC(=O)C(C)C)(=O)C(C)C.C(N1CCC[C@H]1C(O)=O)(=O)CC>>[C:11]([N:80]1[CH2:87][CH2:86][CH2:85][C@H:81]1[C:82]([OH:84])=[O:83])(=[O:10])[CH:76]([CH3:78])[CH3:77]

Participants

Reactant 4

HCID 7346Isobutyric anhydride

HCID 145742L-Proline

HCID 676544(2S)-1-propanoylpyrrolidine-2-carboxylic acid

HCID 13895197HCID 13895197, compound

Product 1

HCID 15324300IsobutyrylprolineYield 96%

Procedure

[Isobutyryl9 ]Didemnin B (33) and [Isobutyryl9, D-Pro8 ] Didemnin B (34). L-Pro (1.15 g, 0.01 mol) was treated with isobutyric anhydride in a procedure like the N-propionylproline synthesis to give N-isobutyrylproline (1.8 g, 96%): fine crystals, mp 80-82° C.; [α]D25 -8.7° (c 1.56, CHCl3). 1H NMR Anal. (C9H15NO3) C, H, N.

Sources & evidence

ORD record: ord-ff17177206504628aeb091ea657000ee
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156724

Reaction notes

Loading…