L-Tartaric acid → HCID 69592662, compound

HRID 1241606Notes

Reaction equation

HRID 1241606 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH2:11]([N:13]([CH2:57][CH3:58])[CH2:14][CH2:15][N:16]([C:31]([CH2:33][N:34]1[CH:39]=[C:38]([CH2:40][C:41]2[CH:42]=[N:43][N:44]([CH3:46])[CH:45]=2)[C:37](=[O:47])[N:36]=[C:35]1[S:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=1)=[O:32])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[CH3:12]>CC(O)C>[OH:8][C:6]([CH:4]([CH:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])=[O:7].[CH2:57]([N:13]([CH2:11][CH3:12])[CH2:14][CH2:15][N:16]([C:31]([CH2:33][N:34]1[CH:39]=[C:38]([CH2:40][C:41]2[CH:42]=[N:43][N:44]([CH3:46])[CH:45]=2)[C:37](=[O:47])[N:36]=[C:35]1[S:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=1)=[O:32])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)[CH3:58]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 23395801HCID 23395801, compound

Product 1

HCID 69592662HCID 69592662, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of L-tartaric acid (0.75 g, 1 equiv) in 2-propanol (12 ml) was added to a solution of the free base from Example 6 (3.43 g, 1 equiv) in 2-propanol (25 ml) with stirring. The mixture was evaporated to ca. one third volume, diluted with ether, then the solid was filtered off, washed with ether and dried in vacuo; yield 3.87 g. 1H-NMR (DMSO, ca. 60:40 rotamer mixture) δ 0.9–1.1 (6H,m), 2.5–2.8 (4H,m), 3.2–3.4 (6H,m), 3.76 (3H,s), 4.20 (2H,s), 4.39/4.43 (2H,2x s), 4.60/4.67 (2H,2x s), 4.92/5.08 (2H,2x s), 7.1–7.7 (15H,m); MS (APCI+) found (M+1)=687/689; C37H40ClFN6O2S requires 686/688.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted with ether
  3. filtrationthe solid was filtered off
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ded4ef12bfa54f17b0f3e129917b69f4
Source dataset
uspto-grants-2006_10
Patent number
US07115616B2

Reaction notes

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