Sodium Carbonate → HCID 16107463, compound

HRID 556217Notes

Reaction equation

HRID 556217 reaction equation
[NH2:1][CH2:2][C:3]([CH2:22][O:23][C:24]([C:33]([F:36])([F:35])[F:34])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])([CH2:7][O:8][C:9]([C:18]([F:21])([F:20])[F:19])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:44]([O:46][CH2:47][CH:48]1[C:60]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[C:54]2[C:49]1=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45]>O1CCCC1.O>[CH:59]1[C:60]2[CH:48]([CH2:47][O:46][C:44]([NH:1][CH2:2][C:3]([CH2:7][O:8][C:9]([C:10]([F:13])([F:12])[F:11])([C:14]([F:17])([F:16])[F:15])[C:18]([F:19])([F:21])[F:20])([CH2:22][O:23][C:24]([C:29]([F:30])([F:31])[F:32])([C:25]([F:26])([F:27])[F:28])[C:33]([F:34])([F:35])[F:36])[C:4]([OH:6])=[O:5])=[O:45])[C:49]3[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:55]=2[CH:56]=[CH:57][CH:58]=1

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 343679-Fluorenylmethyl chloroformateHCID 16107462HCID 16107462, compound

Product 1

HCID 16107463HCID 16107463, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of amino acid 1 (10.1 g, 17.2 mmol) in tetrahydrofuran (100 mL) and water (100 mL) was added sodium carbonate (4.6 g, 42.9 mmol). After all the sodium carbonate was dissolved, the resulting mixture was cooled to 0° C. and 9-fluorenylmethyl chloroformate (6.7 g, 25.9 mol) was added in three portions. The resulted reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuo and the residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=5/1) to give the acid 2 as a white solid (13.3 g, 96%). mp. 104-105° C.; 1H NMR (400 MHz, CD3OD) δ 3.45 (s, 2H), 4.16 (m), 4.27 (m, 4H), 4.46 (d, J=8.8 Hz, 2H) 7.26 (t, J=7.2 Hz, 2H), 7.35 (t, J=7.2 Hz, 2H), 7.60 (d, J=7.6 Hz, 2H), 7.74 (d, J=7.2 Hz, 2H); 19F NMR (376 MHz, CD3OD) δ −71.00 (s); 13C NMR (100.7 MHz, CD3OD) δ 36.9, 42.8, 53.7, 68.2, 69.0, 80.9 (m), 120.9, 121.7 (q, J=292.6 Hz), 126.2, 128.1, 128.8, 142.6, 145.2, 158.8, 174.4; MS (CI) m/z 808 (M++1, 100); HRMS (CI) Calcd for C28H20F18NO6: 808.1003, Found: 808.1010.

Workup

  1. customThe resulted reaction mixture
  2. customThe solvent was removed under vacuo
  3. customthe residue was purified by flash column chromatography on silica gel (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-dec387f66a814fb4a8baebf132606db9
Source dataset
uspto-grants-2011_11
Patent number
US08052961B2

Reaction notes

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