Dicyclohexylcarbodiimide → 4-(3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-1-(2-thioxo-thiazolidin-3-yl)-pentan-1-one

HRID 517662

Reaction equation

HRID 517662 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17](O)[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5](O)=[O:6].C1CCC(N=C=NC2CCCCC2)CC1.[SH:45][C:46]1[S:47][CH2:48][CH2:49][N:50]=1>C(Cl)Cl>[OH:25][CH:23]1[CH2:24][CH:19]2[C:20]([CH3:26])([CH:15]3[CH:16]([CH2:17][CH2:18]2)[CH:11]2[C:12]([CH3:29])([CH:8]([CH:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:50]4[CH2:49][CH2:48][S:47][C:46]4=[S:45])=[O:6])[CH2:9][CH2:10]2)[CH:13]([OH:28])[CH2:14]3)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 221493Cholic AcidHCID 178527880HCID 178527880, compound

Product 1

HCID 866491484-(3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-1-(2-thioxo-thiazolidin-3-yl)-pentan-1-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred solution of cholic acid (1 g, 2.6 mmol) in CH2Cl2 (60 mL) was added DCC (684 mg, 3.6 mmol), 2-mercaptothiazoline (354 mg, 3 mmol), and catalytic amount (40 mg) of N,N-dimethyl amino pyridine (DMAP). The reaction mixture was stirred for 24 h at room temperature at which time the reaction mixture was transferred to a separate-funnel and sequentially washed with 0.5N NaOH solution (100 mL×2), and 0.1N HCl (100 mL×2). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide pure yellow solid 2 (1.07 g, 82%). 1H NMR (CDCl3) δ 0.68 (s, 3H), 0.90 (s, 3H), 0.98 (d, 3H), 1.10-1.95 (m, 23H), 3.25-3.35 (m, 4H), 3.53-3.67 (m, 1H), 3.98 (s, 1H), 4.57 (t, 2H); 13C NMR (CDCl3) δ12.73, 17.49, 23.16, 23.76, 26.17, 27.21, 27.63, 28.33, 28.60, 30.40, 30.74, 33.52, 34.11, 35.32, 35.48, 35.87, 36.00, 36.40, 42.08, 46.52, 47.44, 48.09, 53.59, 56.16, 71.53, 72.99, 175.35, 201.52. HRMS (Positive ion FAB) Calcd for C27H44N3O2 [M+H]+ m/z 494.2763. Found: [M+H]+ m/z 494.2744.

Workup

  1. customwas transferred to a separate-funnel
  2. washsequentially washed with 0.5N NaOH solution (100 mL×2), and 0.1N HCl (100 mL×2)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1343dd02fa142299cf3b69efafde738
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Linked notes

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