Triethylamine → HCID 50924229, compound

HRID 2179771Notes

Reaction equation

HRID 2179771 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:34])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:33])[CH2:12][CH2:13][C@@:14]3([C:30](O)=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:36])[CH3:35])(=[O:3])[CH3:2].C(Cl)(C(Cl)=O)=O.[NH2:43][C@H:44]1[CH2:47][C@@H:46]([C:48]([N:50]2[CH2:54][CH2:53][CH2:52][CH2:51]2)=[O:49])[C:45]1([CH3:56])[CH3:55].CCN(CC)CC>C(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:34])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:33])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:31])[NH:43][C@H:44]4[CH2:47][C@@H:46]([C:48]([N:50]5[CH2:54][CH2:53][CH2:52][CH2:51]5)=[O:49])[C:45]4([CH3:56])[CH3:55])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:36])[CH3:35])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1030053410376-50-8HCID 58110992HCID 58110992, compound2×

Product 1

HCID 50924229HCID 50924229, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (0.3 g, 0.602 mmol) in DCM (1 ml) a solution of (COCl)2 (0.52 ml, 6.02 mmol) in DCM (4 ml) was added at about 0° C. and the reaction mixture was allowed to stir at room temperature for about 3 hours. After completion of the reaction (monitored by TLC), the solvent was evaporated under nitrogen atmosphere and dissolved in DCM (4 ml), which was added to a stirred solution of ((1R,3S)-3-amino-2,2-dimethylcyclobutyl)(pyrrolidin-1-yl)methanone (Intermediate 13, 0.288 g, 1.023 mmol) in DCM (5 ml) and Et3N (0.16 ml, 1.204 mmol) at about 0° C. and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water, 1N HCl, water, brine and dried over Na2SO4, the solvent was evaporated and purified by silica gel column (100-200 mesh, elution 20% EtOAc in hexane) to afford the title compound as an off white solid. Wt: 0.230 g; Yield: 56.5%; 1H NMR (300 MHz, CDCl3): δ 6.38 (d, 1H, J=8.4 Hz), 4.73 (s, 1H), 4.58 (s, 1H), 4.50-4.42 (m, 1H), 4.13-4.02 (m, 1H), 3.56-3.28 (m, 5H), 3.18-3.07 (m, 1H), 2.79 (t, 1H, J=7.2 Hz), 2.55-2.33 (m, 2H), 2.27-2.18 (m, 1H), 2.04 (s, 3H), 2.00-1.74 (m, 8H), 1.72-1.10 (m, 20H), 0.95, 0.92, 0.88, 0.83 (s, 22H); Mass: [M+Na]+ 714 (100%); IR (KBr, cm−1): 3372, 2943, 2864, 1736, 1730, 1652, 1636, 1623, 1501, 1459, 1444, 1369, 1248, 1192, 1024, 979, 881, 853; M.R: 125.4° C.-135.5° C.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe solvent was evaporated under nitrogen atmosphere
  3. dissolutiondissolved in DCM (4 ml)
  4. stirringto stir at room temperature for about 16 hours
  5. customAfter completion of the reaction (monitored by TLC)
  6. washwashed with water, 1N HCl, water, brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was evaporated
  9. custompurified by silica gel column (100-200 mesh, elution 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-3286a0f543bb4846863827a676d638b9
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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