Dimethylformamide → HCID 20610693, compound

HRID 433854Notes

Reaction equation

HRID 433854 reaction equation
CNCC([CH:6]([CH2:10][CH2:11][CH2:12][C@H:13]1[C@@H:21]2[C@@H:16]([NH:17][C:18]([NH:20]2)=[O:19])[CH2:15][S:14]1)C(N)=O)=O.[O:22]=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:36][N:37]([CH:39]=[O:40])[CH3:38].NCC[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([OH:55])=[O:54].C([N:58]([CH2:61]C)[CH2:59][CH3:60])C>C(Cl)(Cl)Cl>[C:39]([N:37]([CH2:38][C:61]([NH:58][CH2:59][CH2:60][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([OH:55])=[O:54])=[O:22])[CH3:36])(=[O:40])[CH2:6][CH2:10][CH2:11][CH2:12][C@H:13]1[C@@H:21]2[C@@H:16]([NH:17][C:18]([NH:20]2)=[O:19])[CH2:15][S:14]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 6966112-Aminododecanoic AcidHCID 131724269HCID 131724269, compound

Product 1

HCID 20610693HCID 20610693, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 4 (32.2 mg, 0.102 mmole) was dried overnight in vacuo (with P2O5). Dry DMF (2 mL) was added and the mixture was stirred with warming to affect dissolution under nitrogen. Triethylamine (34 mcL) was added followed by 1 (20.4 mcL, 0.115 mmole) added in two 10.2 mcL portions, 5 min apart. The mixture was stirred for 1 hr at room temperature under nitrogen. 12-Aminododecanic acid (24.1 mg, 0.112 mmole, Sigma) was added in one portion, and the mixture was stirred at room temperature for 2 hr under nitrogen. CHCl3 (80 mL) was added, and the organic solution was washed with two 10 mL portions of 1 M HCl. CHCl3 was removed by rotary evaporation, and residual DMF was removed by vacuum centrifugation. The compound was dissolved in methanol and purified by HPLC (Vydac 218TP prep column). Solvent program is: 0-10 min, water with 0.06% TFA; 10-55 min, 0-100% methanol with 0.06% TFA, flow rate is 6 mL/min. Yield 31.7 mg. 1H-NMR. ESI-MS, calculated 513.4, observed 513.4 (M+H)+

Workup

  1. temperaturewith warming
  2. dissolutiondissolution under nitrogen
  3. additionadded in two 10.2 mcL portions, 5 min apart
  4. stirringThe mixture was stirred for 1 hr at room temperature under nitrogen
  5. stirringthe mixture was stirred at room temperature for 2 hr under nitrogen
  6. washthe organic solution was washed with two 10 mL portions of 1 M HCl
  7. customCHCl3 was removed by rotary evaporation, and residual DMF
  8. customwas removed by vacuum centrifugation
  9. dissolutionThe compound was dissolved in methanol
  10. custompurified by HPLC (Vydac 218TP prep column)
  11. custom0-10 min, water
  12. custom10-55 min, 0-100% methanol

Sources & evidence

ORD record
ord-e38ac99b60eb4960aa724b213af38f21
Source dataset
uspto-grants-2003_12
Patent number
US06670194B1

Reaction notes

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