Hydrochloric Acid → HCID 23394561, compound

HRID 966410Notes

Reaction equation

HRID 966410 reaction equation
Br[C:2]1[C:5](=[O:6])[C:4]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]=1[NH:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:34])[C:26]2[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=2[Cl:33])=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15].O.Cl.[C:37](OCC)(=[O:39])[CH3:38]>C(N(CC)CC)C>[O:6]=[C:5]1[C:4]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([NH:12][C@@H:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:34])[C:26]3[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=3[Cl:33])=[CH:20][CH:19]=2)[C:14]([O:16][CH2:38][CH2:37][OH:39])=[O:15])=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 10209950HCID 10209950, compound

Product 1

HCID 23394561HCID 23394561, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 2 (31.0 g) was introduced dropwise to a well-stirred solution of Intermediate 16 (50.0 g) in ethyl acetate (500 mL) and triethylamine (25 mL). The reaction temperature was kept below 25° C. throughout by external cooling. Acylation of the starting material was complete after a 1.5 hour stir-out. Water (150 mL) was charged at the end of this period, followed by sufficient 2M hydrochloric acid to lower the pH to 1-1.5. Following separation, the organic phase was washed with water (2×150 mL), 5% sodium carbonate solution (150 mL) and 10% brine (2×150 mL) then dried (MgSO4), filtered and evaporated in vacuo to afford the title compound as a yellow-brown foam (71.1 g, 95.6% yield). 1H NMR D6-DMSO: δ1.1-1.73 (10H, b,m); 2.98 (1H, dd); 3.20 (1H, dd); 3.64 (2H, m); 4.13 (2H, t); 4.24 (1H, m); 4.39 (1H, s); 4.87 (1H, t); 7.28 (2H, d); 7.59 (2H, d); 8.37 (1H, d); 8.81 (2H, s); 10.88 (1H, s) ppm. Mass Spectrum: ESI+ m/z 532/534

Workup

  1. customwas kept below 25° C. throughout by external cooling
  2. customseparation
  3. washthe organic phase was washed with water (2×150 mL), 5% sodium carbonate solution (150 mL) and 10% brine (2×150 mL)
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-33060678f5634c70820c05403352b827
Source dataset
uspto-grants-2005_10
Patent number
US06951943B2

Reaction notes

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