Acetic Acid → HCID 66614898, compound

HRID 2046027Notes

Reaction equation

HRID 2046027 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24](C=O)=[CH:23][C:22]=4[CH:28]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C[CH2:30][N:31]([CH:35](C)C)[CH:32]([CH3:34])C.[BH-]([O:47][C:48](C)=[O:49])(OC(C)=O)OC(C)=O.[Na+].[CH3:52]C(O)=O>ClCCCl.CO.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([CH2:35][N:31]5[CH2:30][CH:34]([C:48]([O:47][CH3:52])=[O:49])[CH2:32]5)=[CH:23][C:22]=4[CH:28]=3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86660602HCID 86660602, compound

Product 1

HCID 66614898HCID 66614898, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture the product of Example 1, Step E (0.07 g; 0.85 mmol), azetidine-3-methylcarboxylate hydrochloride (0.03 g; 0.199 mmol) and DIPEA (0.035 ml, 0.2 mmol) in 1,2-dichloroethane (1 ml) and methanol (MeOH) (3 ml) was sonicated for 30 min at room temperature, then evaporated to dryness. The yellowish residue was suspended in 1,2-dichloroethane (1 ml) and NaBH(OAc)3 (0.12 g; 0.57 mmol) was added, followed by AcOH (0.01 ml). This was stirred for 1 h at room temperature and diluted to 15 ml with EtOAc, washed with 10% KOH (2×3 ml); brine, dried over anhydrous MgSO4, filtered and the filtrate evaporated to dryness. The residue was purified by FCC (SiO2, EtOAc) to give the title compound (0.06 g; 68%), as creamy syrup. 1H-NMR (CDCl3) 8.33 (d, 1H, J=3 Hz); 8.06 (dd, 1H, 3, 9 Hz); 7.78 (dd, 1H, J=3, 9 Hz); 6.87 (d, 1H, J=2 Hz); 6.63 (s, 1H); 4.14-4.22 (m, 4H); 3.6-3.7 (m, 5H); 3.48-3.34 (m, 2H); 1.49 (m, 6H).

Workup

  1. customevaporated to dryness
  2. washwashed with 10% KOH (2×3 ml)
  3. dry with materialbrine, dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness
  6. customThe residue was purified by FCC (SiO2, EtOAc)

Sources & evidence

ORD record
ord-c3ca32653f314d449688447b342b8628
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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