Hydrochloric Acid → HCID 131723700, compound

HRID 2298100Notes

Reaction equation

HRID 2298100 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:25][CH:26]1[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:52]>CO.O1CCOCC1.ClCCCl>[ClH:1].[ClH:52].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:25][CH:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][CH:10]([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27563701-Boc-3-aminopyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 18381537HCID 18381537, compound

Product 1

HCID 131723700HCID 131723700, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to the method described in Example 66c from 2-chloro-5-(2-oxoethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.094 g, Example 66b), 3-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (0.101 g), sodium triacetoxyborohydride (0.081 g) and 1,2-dichloroethane (2 ml). After work-up, the residue was purified by HPLC eluting with a gradient of 0-5% ethanol in dichloromethane. The pale orange powder obtained was dissolved in methanol (2 ml) and a solution of hydrochloric acid in dioxane (4N, 1 ml) was added. The mixture was stirred for 14 h at room temperature. Solvents were then removed under reduced pressure and the product obtained was triturated with diethyl ether to afford the title compound as a pale orange powder (0.033 g).

Workup

  1. customPrepared
  2. customAfter work-up, the residue was purified by HPLC
  3. washeluting with a gradient of 0-5% ethanol in dichloromethane
  4. customThe pale orange powder obtained
  5. customSolvents were then removed under reduced pressure
  6. customthe product obtained
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-af7404a520724596b22c921c33afc9ba
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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