4-Chloroaniline → HCID 58714336, compound

HRID 855591Notes

Reaction equation

HRID 855591 reaction equation
[C:1]([NH:11][C@@H:12]([C:17]([OH:19])=O)[CH2:13][CH2:14][S:15][CH3:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1C=C2N=NN(O)C2=CC=1.O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[Cl:62][C:63]1[CH:69]=[CH:68][C:66]([NH2:67])=[CH:65][CH:64]=1>CN(C)C1C=CN=CC=1.C1COCC1>[Cl:62][C:63]1[CH:69]=[CH:68][C:66]([NH:67][C:17](=[O:19])[C@H:12]([NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[CH2:13][CH2:14][S:15][CH3:16])=[CH:65][CH:64]=1

Participants

8

Reactant 5

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 1712153CBZ-D-MethionineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 58714336HCID 58714336, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

CBZ-d-Methionine (5.4 g, 20 mmol), N-hydroxybenzotriazole H2O (HOBt, 3.0 g, 20 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU, 7.7 g, 20 mmol), 4-(dimethylamino)-pyridine (DMAP, ˜0.020 g, ˜0.16 mmol) and triethylamine (2.8 ml, 20 mmol) were added to a solution of 4-chloroaniline (1.3 g, 10 mmol) in THF. The non-homogeneous solution was stirred at room temperature for 24 hours. The solvent was then removed and the residue taken into ethyl acetate (˜200 ml) and washed sequentially with NaHCO3 (3×100 ml), 10% citric acid (3×100 ml), water (3×100 ml) and saturated NaCl (1×75 ml). The organic layer was then dried with sodium sulfate, filtered, and concentrated to yield (2R)-N-(4-chlorophenyl)-4-methylthio-2-[(phenylmethoxy)carbonylamino]butanamide (M+1=393.26)

Workup

  1. customThe solvent was then removed
  2. washwashed sequentially with NaHCO3 (3×100 ml), 10% citric acid (3×100 ml), water (3×100 ml) and saturated NaCl (1×75 ml)
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1034c896ec054783bfca0e7422f131d8
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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