Sodium Carbonate → HCID 53706509, compound

HRID 1355321Notes

Reaction equation

HRID 1355321 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([OH:15])[CH:7]=1.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].C1C(=O)N(OC(O[CH2:33][CH:34]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44]C=3)[C:40]3[C:35]2=[CH:36][CH:37]=C[CH:39]=3)=O)C(=O)C1.[CH3:47][C:48](C)=O.O>CC(C)=O>[CH:33]1[C:34]2[CH2:46][C:41]3[C:40](=[CH:39][CH:44]=[CH:43][CH:42]=3)[C:35]=2[CH:36]=[CH:37][C:47]=1[CH2:48][O:17][C:16]([NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([OH:15])[CH:7]=1)=[O:19]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 18366337Propan-2-one--water (1/1)HCID 131723943HCID 131723943, compound

Product 1

HCID 53706509HCID 53706509, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The Amino acid (14) (1.864 g; 8 mmol) from Step 2 was dissolved in 1:1 acetone—water (50 mL) containing Sodium Carbonate (1.696 g; 16 mmol). To the solution was added Fmoc-Osu (2.696 g; 8 mmol) in acetone (25 mL) dropwise at room temperature. The solution was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was dissolved in water and extracted with ether (2×50 mL). The aqueous layer was cooled in an ice bath and acidified with 6N HCl to pH 3. The solid obtained was filtered and washed with water and dried under vacuo (3.22 g). NMR (300 MHz, DMSO-d6) δ7.9 (d, 2H), 7.65-7.75 (m, 2H), 7.55 (t, 2H), 7.4 (t, 2H), 7.3 (t, 2H), 6.5 (m, 2H), 4.35 (d, 2H), 4.25 (t, 1H), 4.05 (t, 2H), 3.4 (t, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ether (2×50 mL)
  4. temperatureThe aqueous layer was cooled in an ice bath
  5. customThe solid obtained
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried under vacuo (3.22 g)

Sources & evidence

ORD record
ord-d9959686413749d9af71627939b32030
Source dataset
uspto-grants-2003_07
Patent number
US06586187B1

Reaction notes

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