Oxalic Acid → (r)-2-[4-[2-(t-Butyloxycarbonylamino)propoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene oxalate

HRID 1387110Notes

Reaction equation

HRID 1387110 reaction equation
N(C(OCC)=O)=N[C:3](OCC)=[O:4].C1(P([C:26]2[CH:31]=[CH:30]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[S:43][C:42]3[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=3[C:40]=2[CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH2:57][N:58]3[CH2:62][CH2:61][CH2:60][CH2:59]3)=[CH:51][CH:50]=2)=[CH:35][CH:34]=1.[NH4+:63].[OH-:64].[C:65]([OH:70])(=[O:69])[C:66]([OH:68])=[O:67].[CH2:71]1[CH2:75]OC[CH2:72]1>C(Cl)(Cl)Cl.CO>[C:65]([OH:70])(=[O:69])[C:66]([OH:68])=[O:67].[C:71]([O:64][C:3]([NH:63][C@H:31]([CH3:30])[CH2:26][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[S:43][C:42]3[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=3[C:40]=2[CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH2:57][N:58]3[CH2:59][CH2:60][CH2:61][CH2:62]3)=[CH:51][CH:50]=2)=[CH:35][CH:34]=1)=[O:4])([CH3:72])([CH3:75])[CH3:65]

Participants

9

Reactant 6

HCID 971Oxalic AcidHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 14923Ammonium HydroxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 224626554-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenol

Product 1

HCID 69697070(r)-2-[4-[2-(t-Butyloxycarbonylamino)propoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene oxalateYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6212ChloroformSolvent

Procedure

By essentially following the conditions described in Example 20, Part B, adding the diethyl azodicarboxylate to a mixture of triphenylphospine, 2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (Part A) and (R)-(−)-N-t-Boc-2-amino-1-propanol (Part B) in THF at 0° C. and stirring the reaction mixture at ambient temperature about 16 h, the free base of the title compound was prepared as a foam in 65% yield following flash chromatography (SiO2; 1% then 3% then 5% MeOH in CHCl3 sat'd with NH4OH). The foam was taken up in a minimal amount of MeOH and treated with a solution of oxalic acid in MeOH to provide the oxalate salt.

Sources & evidence

ORD record
ord-db4e9d4fee584d3bb1df94b838577771
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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