Hydrochloric Acid → HCID 68680654, compound

HRID 2261279Notes

Reaction equation

HRID 2261279 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[N:7]([C:10](=[O:34])[C@@H:11]([NH:16]C(=O)C3C=CC(N4CCN(CCC)CC4)=CC=3)[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH2:9][C@H:5]2[O:4][CH2:3]1.[ClH:35].O1CCOCC1.O[C@@H]1[C@H]2N(C(=O)[C@@H](NC(=O)OC(C)(C)C)CC(C)C)CC[C@H]2OC1>>[ClH:35].[NH2:16][C@@H:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:10]([N:7]1[CH2:8][CH2:9][C@H:5]2[O:4][CH2:3][C@H:2]([OH:1])[C@@H:6]12)=[O:34]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68345507HCID 68345507, compoundHCID 86633304HCID 86633304, compound

Product 1

HCID 68680654HCID 68680654, compound

Procedure

Preparation of N—((S)-1-((3R,3aR,6aR)-3-Hydroxydihydro-2H-furo[3,2-b]pyrrol-4(5H, 6H,6aH)-yl)-4-methyl-1-oxopentan-2-yl)-4-(4-propylpiperazin-1-yl)benzamide A solution of HCl in 1,4-dioxane (4.0M, 22 mL, 88 mmol) was added to tert-butyl(S)-1-((3R,3aR,6aR)-3-hydroxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4-methyl-1-oxopentan-2-ylcarbamate (1.335 g, 3.90 mmol). The solution was stirred for 2.5 hours then the solvents were removed in vacuo and the residue azeotroped with toluene (3×30 mL) to leave (S)-2-amino-1-((3R,3aR,6aR)-3-hydroxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4-methylpentan-1-one hydrochloride as an off-white solid which was used without further purification. TLC (Rf=0.0, EtOAc:heptane 3:1), analytical HPLC main peak, Rt=3.54 min., HPLC-MS 243.2 [M+H]+, 507.3 [2M+Na]+.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue azeotroped with toluene (3×30 mL)

Sources & evidence

ORD record
ord-872e1b17120f4a49a5b2c92faf8e869d
Source dataset
uspto-grants-2010_12
Patent number
US07846935B2

Reaction notes

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