Diisopropylethylamine → HCID 58746487, compound

HRID 724737Notes

Reaction equation

HRID 724737 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[C:16]([F:28])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[NH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][O:72][C:73]1[CH:82]=[CH:81][CH:80]=[C:79]([OH:83])[C:74]=1[C:75]([O:77][CH3:78])=[O:76]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:24](=[O:25])(=[O:26])[NH:23][C:22](=[O:27])[CH2:21]2)=[C:16]([F:28])[CH:15]=1)[C:10]([NH:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][O:72][C:73]1[CH:82]=[CH:81][CH:80]=[C:79]([OH:83])[C:74]=1[C:75]([O:77][CH3:78])=[O:76])=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21878568HCID 21878568, compoundHCID 58746818HCID 58746818, compound

Product 1

HCID 58746487HCID 58746487, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S)-2-[(tert-Butoxycarbonyl)amino]-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorophenyl]propanoic acid (16.7 mg, 0.0400 mmol) in DMF (2.00 mL) was treated with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (19.5 mg, 0.044 mmol). After five minutes N,N-diisopropylethylamine (20.9 μL, 0.120 mmol) and methyl 2-[(5-aminopentyl)oxy]-6-hydroxybenzoate hydrochloride (14.5 mg, 0.050 mmol) were added and the solution stirred at rt for 1 h. The product was directly purified by preparative LCMS to afford product as a white solid (17.8 mg, 68%). 1H NMR (400 MHz, CD3OD): δ 7.45–7.42 (m, 1H), 7.24–7.21 (m, 1H), 7.16–7.10 (m, 2H), 6.50–6.45 (m, 2H), 5.37–5.34 (m, 1H), 4.27–4.24 (m, 1H), 3.97 (t, J=6.3 Hz, 2H), 3.87 (s, 3H), 3.42–3.05 (m, 7H), 2.99–2.94 (m, 1H), 1.79–1.75 (m, 2H), 1.47–1.40 (m, 4H), 1.36 (s, 9H). LCMS found for C30H39FN3O10S (M+H)+: m/z=652.

Workup

  1. customThe product was directly purified by preparative LCMS

Sources & evidence

ORD record
ord-8f095f53ccae4b39915ccd93d905f456
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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