Diisopropylethylamine → HCID 58746780, compound

HRID 724673Notes

Reaction equation

HRID 724673 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:16][C@H:17]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:18]([OH:20])=O)[CH:5]=[CH:6][C:7]=1[CH:8]1[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]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.[C:58]1([CH2:64][CH2:65][CH2:66][CH2:67][NH2:68])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:16][CH:17]([NH:21][S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:23])=[O:24])[C:18]([NH:68][CH2:67][CH2:66][CH2:65][CH2:64][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:20])[CH:5]=[CH:6][C:7]=1[CH:8]1[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 83242BenzenebutanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58746551HCID 58746551, compound

Product 1

HCID 58746780HCID 58746780, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(2S)-3-[3-chloro-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-2-[(phenylsulfonyl)-amino]propanoic acid (15.0 mg, 0.0317 mmol) in DMF (1 mL) was treated with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (16.8 mg, 0.0381 mmol) and stirred at rt for 5 minutes. A solution of 4-phenylbutan-1-amine (10 μL, 0.0634 mmol) and N,N-diisopropylethylamine (28 μL, 0.16 mmol) in DMF (1 mL) was added and the reaction stirred at rt for 1 h. Purification by preparative LCMS afforded product as a white solid (12.9 mg, 67%). 1H NMR (400 MHz, CD3OD): δ 7.68–7.64 (m, 2H), 7.54–7.34 (m, 4H), 7.27–7.11 (m, 7H), 5.59–5.57 (m, 1H), 3.92–3.87 (m, 1H), 3.42–3.35 (m, 1H), 3.35–3.28 (m, 1H), 2.99–2.84 (m, 3H), 2.79–2.74 (m, 1H), 2.56 (t, J=7.5 Hz, 2H), 1.53–1.47 (m, 2H), 1.33–1.29 (m, 2H); LCMS found for C28H31ClN3O6S2 (M+H)+: m/z=604.

Workup

  1. stirringthe reaction stirred at rt for 1 h
  2. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-9ce3e291b4a840ae8fa7d1a251cb7f93
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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