Diisopropylcarbodiimide → HCID 18374603, compound

HRID 2300709Notes

Reaction equation

HRID 2300709 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:11](=[O:20])[CH:10]2[CH2:21][CH2:22][CH:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[OH:24])=[CH:5][CH:4]=1.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[CH2:39]([C:43]1([CH2:77][CH3:78])[CH2:49][S:48](=[O:51])(=[O:50])[C:47]2[CH:52]=[CH:53][C:54]([N:56]([CH3:58])[CH3:57])=[CH:55][C:46]=2[CH:45]([C:59]2[CH:60]=[C:61]([NH:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][C:73](O)=[O:74])[CH:62]=[CH:63][CH:64]=2)[CH:44]1[OH:76])[CH2:40][CH2:41][CH3:42].C(N=C=NC(C)C)(C)C.OC1C2N=NNC=2C=CC=1>CN(C)C=O.C(N(CC)CC)C>[F:32][C:33]([F:38])([F:37])[C:34]([O-:36])=[O:35].[CH2:39]([C:43]1([CH2:77][CH3:78])[CH2:49][S:48](=[O:51])(=[O:50])[C:47]2[CH:52]=[CH:53][C:54]([NH+:56]([CH3:58])[CH3:57])=[CH:55][C:46]=2[CH:45]([C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([NH:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][C:73](=[O:74])[NH:1][CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH:9]4[CH:10]([CH2:21][CH2:22][CH:23]([C:25]5[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)[OH:24])[C:11](=[O:20])[N:12]4[C:13]4[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=4)=[CH:5][CH:4]=3)[CH:60]=2)[CH:44]1[OH:76])[CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 222520324-(4-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-oneHCID 171929744HCID 171929744, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 18374603HCID 18374603, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

55 mg of 4-(4-aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one are added to a solution of 40 mg of (2-{2-[3-(3-butyl-7-dimethylamino-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1H-benzo[b]thiepin-5-yl)phenylamino]ethoxy}ethoxy)acetic acid compound with trifluoroacetic acid, 37 μl of diisopropylcarbodiimide, 26 mg of hydroxybenzotriazole and 40 μl of triethylamine in 2 ml of dimethylformamide, and the mixture is stirred for 12 h. The reaction solution is concentrated and separated by HPLC (Merck-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90).

Workup

  1. concentrationThe reaction solution is concentrated
  2. customseparated by HPLC (Merck-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

Sources & evidence

ORD record
ord-109a1adc11af468ab747e0f650c543b5
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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