Diisopropylethylamine → 2-(acetylamino)-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-N-(4-phenylbutyl)propanamide

HRID 724638Notes

Reaction equation

HRID 724638 reaction equation
C(O[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])[N:23](C(C)(C)C)[C:22](=[O:31])[CH2:21]2)=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])(C)(C)C.[CH:32](N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[C:65]1([CH2:71][CH2:72][CH2:73][CH2:74][NH2:75])[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C)C=O>[C:6]([NH:8][CH: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:31])[CH2:21]2)=[CH:16][CH:15]=1)[C:10]([NH:75][CH2:74][CH2:73][CH2:72][CH2:71][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:12])(=[O:7])[CH3:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 83242BenzenebutanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11568707(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid

Product 1

HCID 724104302-(acetylamino)-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-N-(4-phenylbutyl)propanamideYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid (12 mg, 0.035 mmol) in N,N-dimethylformamide (1.0 mL) was added N,N-diisopropylethylamine (0.018 mL, 0.10 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (16 mg, 0.042 mmol) and premixed for 5 minutes. 4-phenylbutan-1-amine (6.3 mg, 0.042 mmol) was added and the mixture was stirred for 2 h. The product was purified by preparative LCMS to afford the final product (6.8 mg, 41%). 1H NMR (500 MHz, CD3OD): δ 7.41 (d, J=8.3 Hz, 2H), 7.33 (d, J=8.3 Hz, 2H), 7.25–7.27 (m, 2H), 7.15–7.20 (m, 4H), 5.08–5.12 (m, 1H), 4.54–4.58 (m, 1H), 3.18–3.31 (m, 1H), 3.07–3.17 (m, 3H), 2.93–2.97 (m, 1H), 2.59–2.68 (m, 2H), 1.94 (s, 3H), 1.51–1.59 (m, 2H), 1.41–1.46 (m, 2H); LCMS found for C24H30N3O5S (M+H)+: m/z=472.2

Workup

  1. additionpremixed for 5 minutes
  2. customThe product was purified by preparative LCMS

Sources & evidence

ORD record
ord-86bdd27746a84377a3385d818f27cd8a
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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