Diisopropylethylamine → HCID 56953688, compound

HRID 1630077Notes

Reaction equation

HRID 1630077 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:34][C:35]1[CH:49]=[CH:48][C:38]([O:39][C:40]2[CH:41]=[C:42]([NH2:47])[C:43]([NH2:46])=[CH:44][CH:45]=2)=[CH:37][CH:36]=1.[CH2:50]([O:57][CH2:58][C@H:59]([NH:63][C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C:60](O)=[O:61])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:47][C:42]1[CH:41]=[C:40]([O:39][C:38]2[CH:48]=[CH:49][C:35]([F:34])=[CH:36][CH:37]=2)[CH:45]=[CH:44][C:43]=1[NH:46][C:60](=[O:61])[C@@H:59]([NH:63][C:64](=[O:65])[O:66][C:67]([CH3:68])([CH3:69])[CH3:70])[CH2:58][O:57][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58118725HCID 58118725, compound

Product 1

HCID 56953688HCID 56953688, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step (c) DIEA (0.88 mL, 5.10 mmol) and HATU (750 mg, 2 mmol) were added to a stirred solution of 4-(4-fluorophenoxy)benzene-1,2-diamine (370 mg, 1.7 mmol), (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid (550 mg, 1.86 mmol) and DMF (4 mL) at ambient temperature. The mixture was stirred for 1 hour and then aqueous saturated sodium bicarbonate solution (8 mL) was added. The resulting solution was extracted with ethyl acetate (4×2 mL) and the combined extract was dried over magnesium sulfate and concentrated. Product was purified from the residue by silica gel column chromatography (eluting with a 3:1→2:1 mixture of hexane/EtOAc) to give (S)-tert-butyl 1-(2-amino-4-(4-fluorophenoxy)phenylamino)-3-(benzyloxy)-1-oxo-propan-2-ylcarbamate (610 mg, 72%) as a brown foam.

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate (4×2 mL)
  2. extractionthe combined extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated
  5. customProduct was purified from the residue by silica gel column chromatography (
  6. washeluting with a 3:1→2:1 mixture of hexane/EtOAc)

Sources & evidence

ORD record
ord-f4da4058659a49459a2e3c9af730093c
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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