Formaldehyde → HCID 69284554, compound

HRID 2225293Notes

Reaction equation

HRID 2225293 reaction equation
[CH:1]([NH:4][C@H:5]1[CH2:10][C@@H:9]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[C@@H:8]([NH:17][C:18](=[O:33])[CH2:19][NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:7][CH2:6]1)([CH3:3])[CH3:2].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:38](C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[CH:1]([N:4]([CH3:38])[C@H:5]1[CH2:10][C@@H:9]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[C@@H:8]([NH:17][C:18](=[O:33])[CH2:19][NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:7][CH2:6]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 69286125HCID 69286125, compound

Product 1

HCID 69284554HCID 69284554, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,2S,5R)-isopropyl 5-(isopropylamino)-2-(2-(3-trifluoromethyl-benzamido)acetamido)cyclohexanecarboxylate (210 mg, 0.45 mmol; Example 11l) in 10 ml of CH2Cl2 is treated with 37% aqueous formaldehyde (0.5 ml) and NaBH(OAc)3 (0.3 g, 1.4 mmol) powder and stirred at room temperature for 2 hours. The mixture was treated with 1 N NaOH and stirred at room temperature for 1 hr and extracted into CH2Cl2. The extract was washed with water, brine, dried over Na2SO4, filtered and the solvent evaporated to give 200 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ(TMS): 8.16 (s, 1 H), 8.06 (d, J=7.8 Hz, 1 H), 7.86 (bt, 1 H), 7.75 (d, J=7.8 Hz, 1 H), 7.55 (t, J=7.8 Hz, 1 H), 7.21 (bs, 1 H), 4.91 (m, 1 H), 4.51 (m, 1 H), 4.12 (d, J=5.2 Hz, 2 H), 3.01 (m, 1 H), 2.58 (m, 1 H), 2.57 (m, 2 H), 2.21 (s, 3 H), 2.02-1.40 (m, 7 H), 1.16 (m, 6 H), 1.02 (m, 6 H). MS found: (M+H)+=486.46.

Workup

  1. stirringstirred at room temperature for 1 hr
  2. extractionextracted into CH2Cl2
  3. washThe extract was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-30586484347643b08b59d0a7ec0410fe
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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