Hydrochloric Acid → HCID 131729089, compound

HRID 1670614Notes

Reaction equation

HRID 1670614 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][C@@H:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[N+:22]([O-:24])=[O:23])[CH2:11][C@H:10]1[CH2:25][OH:26])=O)(C)(C)C>O1CCOCC1.ClCCl>[ClH:1].[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C@@H:12]2[CH2:13][NH:9][C@H:10]([CH2:25][OH:26])[CH2:11]2)=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57748729HCID 57748729, compound

Product 1

HCID 131729089HCID 131729089, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4.0 M hydrogen chloride in dioxane (950 mL) slowly to a solution of (2S,4S)-4-(4-bromo-2-nitro-phenylamino)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.22 mol, 95 g) in dry dichloromethane (475 mL) at room temperature and stir for 2 h. Filter the precipitated solid and dry under vacuum to obtain the title compound (70 g, 87%) as an orange solid. 1H NMR (400 MHz, CD3OD) δ 1.98-2.05 (m, 1H), 2.71-2.79 (m, 1H), 3.36 (dd, 1H), 3.58-3.63 (m, 1H), 3.76 (dd, 1H), 3.88-3.95 (m, 2H), 4.55-4.58 (m, 1H), 7.03 (d, 1H), 7.66 (dd, 1H), 8.30 (d, 1H).

Workup

  1. filtrationFilter the precipitated solid
  2. customdry under vacuum

Sources & evidence

ORD record
ord-57529bead3b54eaaa49e43897864a66c
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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