Acetic Acid → HCID 69918360, compound

HRID 2307791Notes

Reaction equation

HRID 2307791 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]([CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=2)[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[BH3-]C#N.[Na+].CC(O)=O>CO.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C@@H:8]([CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:21][CH:22]=2)[CH:16]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 88052524HCID 88052524, compound

Product 1

HCID 69918360HCID 69918360, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 116A (0.03 g, 0.06 mmol) in 2 mL of MeOH was cooled to 0° C. then treated with aniline (0.018 g 0.2 mmol), NaBH3CN (0.004 g, 0.06 mmol) and AcOH (1 ml). The mixture was allowed to warm to room temperature overnight. The mixture was diluted with ethyl acetate (20 ml), washed with water (10 ml) and brine (10 ml). The ethyl acetate was evaporated off and the residue was used without further purification.

Workup

  1. washwashed with water (10 ml) and brine (10 ml)
  2. customThe ethyl acetate was evaporated off
  3. customthe residue was used without further purification

Sources & evidence

ORD record
ord-8c98824c55784558a54e4339caf53ae4
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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