Acetone → 1-[(S)-2-[[[1-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]hydroxyphosphinyl]oxyl]-1-oxopropyl]-L-proline, ethyl ester

HRID 231945Notes

Reaction equation

HRID 231945 reaction equation
[CH3:1]N(C)C.N#N.[C:7]([NH:15][C@H:16]([C:32](O)=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20]NC(OCC1C=CC=CC=1)=O)(=[O:14])C1C=CC=CC=1.FC(F)(F)C(NCCC[CH2:43][C@H:44]([O:57][P:58]([CH:62]([NH2:67])[CH2:63][CH2:64][CH2:65][CH3:66])([O:60]C)=[O:59])[C:45]([N:47]1[CH2:56][CH2:55][CH2:54][C@H:48]1[C:49]([O:51][CH2:52][CH3:53])=[O:50])=[O:46])=O.N.[CH3:71][C:72]([CH3:74])=[O:73]>O.C(O)(C)C>[CH3:71][C:72]([CH3:1])([O:73][C:7]([NH:15][C@@H:16]([CH2:17][CH2:18][CH2:19][CH3:20])[C:32]([NH:67][CH:62]([P:58]([O:57][C@@H:44]([CH3:43])[C:45]([N:47]1[CH2:56][CH2:55][CH2:54][C@H:48]1[C:49]([O:51][CH2:52][CH3:53])=[O:50])=[O:46])([OH:60])=[O:59])[CH2:63][CH2:64][CH2:65][CH3:66])=[O:33])=[O:14])[CH3:74]

Participants

8

Reactant 5

HCID 180AcetoneHCID 222AmmoniaHCID 1146TrimethylamineHCID 1317160031-[(S)-6-[(Trifluoroacetyl)amino]-2-[[[(1-amino)pentyl]methoxyphosphinyl]oxy]-1-oxohexyl]-L-proline, ethyl esterHCID 131716011N2 Benzoyl-N6-[(phenylmethoxy)carbonyl]-L-lysine

Product 1

HCID 1317160101-[(S)-2-[[[1-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]hydroxyphosphinyl]oxyl]-1-oxopropyl]-L-proline, ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Trimethylamine is bubbled into a solution of the diester product from part (a) (483 mg., 0.86 mmole) in acetone (6 ml.) according to the procedure of Example 4 part (f) to yield 432 mg. of 1-[(S)-2-[[[1-[[(S)-2-[[(1,1-dimethylethoxycarbonyl]amino]-1-oxohexyl]amino]pentyl]hydroxyphosphinyl]oxyl]-1-oxopropyl]-L-proline, ethyl ester (isomer B). TLC (silica gel; isopropanol:ammonia:water, 7:2:1) Rf =0.60.

Workup

  1. customto yield 432 mg

Sources & evidence

ORD record
ord-dd1ac6a0e1e3482081438fa6c00764e7
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

Loading…