Ammonia → HCID 86743242, compound

HRID 231943Notes

Reaction equation

HRID 231943 reaction equation
[OH-].[Li+].OC(CCCCNC(=O)C(F)(F)F)C(N1CCC[C@H]1C(OCC)=O)=O.FC(F)(F)C(NCCC[CH2:36][C@H:37]([O:50][P:51]([CH:55]([NH:60][C:61](=[O:85])[C@@H:62]([NH:78][C:79]([CH:81]1C[CH2:83][CH2:82]1)=[O:80])[CH2:63][CH2:64][CH2:65][CH2:66][NH:67][C:68]([O:70][CH2:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)=[O:69])[CH2:56][CH2:57][CH2:58][CH3:59])([O:53]C)=[O:52])[C:38]([N:40]1[CH2:49][CH2:48][CH2:47][C@H:41]1[C:42]([O:44]CC)=[O:43])=[O:39])=O.N>O1CCOCC1.O.C(O)(C)C>[C:72]1([CH2:71][O:70][C:68]([NH:67][CH2:66][CH2:65][CH2:64][CH2:63][C@H:62]([NH:78][C:79]([CH:81]2[CH2:82][CH2:83]2)=[O:80])[C:61]([NH:60][CH:55]([P:51]([OH:53])([O:50][C@@H:37]([CH3:36])[C:38]([N:40]2[CH2:49][CH2:48][CH2:47][C@H:41]2[C:42]([OH:44])=[O:43])=[O:39])=[O:52])[CH2:56][CH2:57][CH2:58][CH3:59])=[O:85])=[O:69])[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 3939Lithium HydroxideHCID 131716005HCID 131716005, compoundHCID 131716006HCID 131716006, compound

Product 1

HCID 86743242HCID 86743242, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1N Lithium hydroxide (10 ml.) is added to a solution of the ethyl ester product from part (c) (800 mg., 1.15 mmole) in p-dioxane (10 ml.) and the reaction mixture is worked up according to the procedure of Example 4 part (g) to yield 670 mg. of 1-[(S)-2-[[[1-[[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-[(cyclopropylcarbonyl)amino]-1-oxohexyl]amino]pentyl]hydroxyhosphinyl]oxy]-1-oxopropyl]-L-proline (isomer B). TLC (silica gel; isopropanol: ammonia:water, 7:2:1) Rf =0.43.

Workup

  1. customto yield 670 mg

Sources & evidence

ORD record
ord-ae986483a1684460ba310babf582b290
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

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