Diisopropylethylamine → Methyl 2-[4-((2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoylamino)butoxy]-6-hydroxybenzoate

HRID 724710Notes

Reaction equation

HRID 724710 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]2)=[CH:19][CH:18]=1)[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:58][CH2:59][CH2:60][CH2:61][CH2:62][O:63][C:64]1[CH:73]=[CH:72][CH:71]=[C:70]([OH:74])[C:65]=1[C:66]([O:68][CH3:69])=[O:67].C(N(CC)C(C)C)(C)C>C(#N)C.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]2)=[CH:19][CH:18]=1)[C:13]([NH:58][CH2:59][CH2:60][CH2:61][CH2:62][O:63][C:64]1[CH:73]=[CH:72][CH:71]=[C:70]([OH:74])[C:65]=1[C:66]([O:68][CH3:69])=[O:67])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11832643Methyl 2-(4-aminobutoxy)-6-hydroxybenzoateHCID 58746775(2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid

Product 1

HCID 58746718Methyl 2-[4-((2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoylamino)butoxy]-6-hydroxybenzoateYield 31.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid (10 mg, 23.1 μmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (10.7 mg, 24.3 μmol) and N,N-dimethylformamide (1 mL) was stirred at 0° C. After stirring for 15 min, methyl 2-(4-aminobutoxy)-6-hydroxybenzoate (6.09 mg, 25.4 μmol) and N,N-diisopropylethylamine (12.1 μL) were added to the reaction. The resulting mixture was stirred at 25° C. for 3 h. The reaction solution was diluted with acetonitrile and purified by preparative LCMS to yield the desired product (4.7 mg, 31%). MF=C32H35N3O10S; LCMS found for C32H36N3O10S (M+H)+: m/z=654.

Workup

  1. stirringThe resulting mixture was stirred at 25° C. for 3 h
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-22f3b2b6299b432c8824c3da8e360f36
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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