Triethylamine → HCID 21920670, compound

HRID 1244670Notes

Reaction equation

HRID 1244670 reaction equation
[NH2:1][C:2]1([C:15]([OH:17])=[O:16])[CH2:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH2:4][CH2:3]1.C1C(=O)N([O:25][C:26]([O:28][CH2:29][CH:30]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]3[C:31]2=[CH:32][CH:33]=[CH:34][CH:35]=3)=O)C(=O)C1.CCN(CC)CC>[OH-].[Na+].C(#N)C.C(#N)C.O>[CH:41]1[C:42]2[CH:30]([CH2:29][O:28][C:26]([NH:1][C:2]3([C:15]([OH:17])=[O:16])[CH2:14][C:13]4[C:12]5[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=5)[NH:6][C:5]=4[CH2:4][CH2:3]3)=[O:25])[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]=2[CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 219206413-Amino-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

Product 1

HCID 21920670HCID 21920670, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 14798Sodium HydroxideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

26 mmol (5.8 g) of 3-amino-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid in 26 ml of 1N NaOH and 26 mmol (8.76 g) of Fmoc-ONSu in 28 ml of acetonitrile are combined at room temperature and diluted with 130 ml of acetonitrile/H2O 1:1. After two hours, the pH is readjusted to 9 (1.5 ml) with NEt3 and stirred overnight at room temperature. Then, another 6.3 g (18.7 mmol) of Fmoc-ONSu, dissolved in 19 ml of acetonitrile, is added and stirred for another two hours while the pH is monitored. After distillative removal of the acetonitrile, it is acidified with 0.01 M HCl and extracted with ethyl acetate. The extract is washed neutral, dried with Na2SO4 and spun in until a dry state is reached. Recrystallization is carried out from ether/hexane. Yield: 10.7 g.

Workup

  1. customare combined at room temperature
  2. additionis added
  3. stirringstirred for another two hours while the
  4. customAfter distillative removal of the acetonitrile, it
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed neutral
  7. dry with materialdried with Na2SO4
  8. customRecrystallization

Sources & evidence

ORD record
ord-b8e9206d866947788d41385b133de5a2
Source dataset
uspto-grants-2006_10
Patent number
US07122570B2

Reaction notes

Loading…