HCID 86669982, compound → HCID 67150294, compound

HRID 1475133Notes

Reaction equation

HRID 1475133 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@@H:6]1[CH2:24][CH2:25][P:26](=[O:29])([O-:28])[O-:27])(=O)C.[CH2:30]([NH+:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH3:31].[CH2:37]([NH+:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH3:38]>O.CO.CCN(CC)CC>[C@H:6]1([CH2:24][CH2:25][P:26](=[O:27])([O-:29])[O-:28])[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4].[CH2:30]([NH+:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH3:31].[CH2:37]([NH+:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH3:38]

Participants

3

Reactant 1

HCID 86669982HCID 86669982, compound

Product 1

HCID 67150294HCID 67150294, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 6 (49.3 mg, 0.11 mmol) in H2O/MeOH/Et3N (7:3:1, 11 mL) was stirred for 16 h at room temperature. The reaction was evaporated to dryness and the residual white powder was purified by Purification Method 1 (100% 0.05 M TEAB) to afford the triethylammonium salt of 7 as a colorless foam (30 mg, 99%): Rf 0.2 (iPrOH/H2O/aq. NH4OH 6:3:1); δH (400 MHz, D2O) 3.82-3.70 (m, 3H, H-3, H-6, H-7), 3.59 (dd, 1H, J1,2 3.4 Hz, J2,3 9.5 Hz, H-4), 3.54-3.43 (m, 3H, H-5, H-8a, H-8b), 2.97 (q, J=7.3 Hz, NCH2CH3, 1.4 equiv.), 1.70-1.20 (m, 4H, H-1a, H-1b, H-2a, H-2b), 1.04 (t, J=7.3 Hz, NCH2CH3, 1.4 equiv.); δC (100 MHz, D2O) 76.2 (d, JC,P 16.3 Hz, C-3), 71.6 (C-7), 69.6, 69.2 (C-5/C-6), 68.3 (C-4), 61.3 (C-8), 46.7 (NCH2CH3), 23.9 (d, JC,P 134.2 Hz, C-1), 18.4 (C-2), 8.3 (NCH2CH3); δP (161.9 MHz, D2O) 24.9. m/z (ESI) 271.0590 [M−H]−, C8H16O8P requires 271.0588.

Workup

  1. customThe reaction was evaporated to dryness
  2. customthe residual white powder was purified by Purification Method 1 (100% 0.05 M TEAB)

Sources & evidence

ORD record
ord-5878864df55f4907bc0390ba991627e5
Source dataset
uspto-grants-2015_04
Patent number
US09018370B2

Reaction notes

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