Isopropylamine → HCID 69386027, compound

HRID 916831Notes

Reaction equation

HRID 916831 reaction equation
[CH3:1][C:2]1([CH3:40])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:39]=[CH:38][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]5[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=5)[C:32](O)=[O:33])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[CH:41]([NH2:44])([CH3:43])[CH3:42].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1([CH3:40])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:39]=[CH:38][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]5[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=5)[C:32]([NH:44][CH:41]([CH3:43])[CH3:42])=[O:33])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69390964HCID 69390964, compound

Product 1

HCID 69386027HCID 69386027, compoundYield 115.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-{[2-(4-{2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}benzoic acid (90 mg) and isopropyl amine (9.7 mg) in DMF (2 ml) was cooled to 0° C. and treated with diisopropylethylamine (0.057 ml) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (62 mg). This was then stirred for 8 h before diluting in EtOAc and washing sequentially with 2M HCl, NaHCO3 (aq) and brine. The combined organic layers were then dried (MgSO4) and concentrated in vacuo to give the title compound(112 mg). LCMS RT=3.36 min.

Workup

  1. washwashing sequentially with 2M HCl, NaHCO3 (aq) and brine
  2. dry with materialThe combined organic layers were then dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4812832da9774a7e918a71aef799a381
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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