Diisopropylethylamine → HCID 20659577, compound

HRID 1371293Notes

Reaction equation

HRID 1371293 reaction equation
[C:1]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[O:18][CH2:19][C:20](O)=[O:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:24][O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:31])[CH3:30])[NH2:28].N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.C(Cl)Cl>[CH3:24][O:25][C:26](=[O:32])[C@H:27]([CH:29]([CH3:31])[CH3:30])[NH:28][C:20](=[O:21])[CH2:19][O:18][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111190Methyl valinate hydrochlorideHCID 4641409(Dimethylamino)-N,N-dimethyl(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yloxy)methaniminiumHCID 21197506HCID 21197506, compound

Product 1

HCID 20659577HCID 20659577, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (2-carbo-tert-butoxy-1-naphthyloxy)acetic acid (1.20 g, 3.97 mmol, see Example 165, Part A) and valine methyl ester hydrochloride (0.932 g, 5.56 mmol) in N-methylpyrrolidone(7.5 mL)-CH2Cl2(7.5 mL) at room temperature under nitrogen was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophate (2.11 g, 5.56 mmol) and diisopropylethylamine (2.42 mL, 13.9 mmol). After stirring at room temperature for 3.5 hrs, the mixture was partitioned between EtOAc-water. The organic phase was washed with water, 5% KHSO4, saturated NaHCO3 and saturated NaCl solutions, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with EtOAc-hexane (1:9 to 3:7) to give the title compound (1.40 g, 85%) as a colorless oil. TLC(EtOAc-hexane; 1:1) Rf=0.76.

Workup

  1. customat room temperature
  2. customthe mixture was partitioned between EtOAc-water
  3. washThe organic phase was washed with water, 5% KHSO4, saturated NaHCO3 and saturated NaCl solutions
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc-hexane (1:9 to 3:7)

Sources & evidence

ORD record
ord-48f064a0639a4a24b81a760bc76ededc
Source dataset
uspto-grants-2007_01
Patent number
US07157430B2

Reaction notes

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