Hydrochloric Acid → (S)-2-amino-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethylpentan-1-one hydrochloride

HRID 1716467Notes

Reaction equation

HRID 1716467 reaction equation
[ClH:1].O1CCOCC1.[OH:8][C@@H:9]1[C@H:13]2[N:14]([C:19](=[O:34])[C@@H:20]([NH:26]C(=O)OC(C)(C)C)[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][C@@H:16]([O:17][CH3:18])[C@H:12]2[O:11][CH2:10]1>>[ClH:1].[NH2:26][C@@H:20]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([N:14]1[CH2:15][C@@H:16]([O:17][CH3:18])[C@H:12]2[O:11][CH2:10][C@H:9]([OH:8])[C@@H:13]12)=[O:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86633075tert-butyl (S)-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-ylcarbamate

Product 1

HCID 68506208(S)-2-amino-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethylpentan-1-one hydrochloride

Procedure

A solution of HCl in 1,4-dioxane (4.0M, 25 mL, 100 mmol) was added to tert-butyl (S)-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-ylcarbamate (1.73 g, 4.48 mmol). The solution was stirred for 2 hours then the solvents were removed in vacuo and the residue azeotroped with toluene (1×50 mL then 1×25 mL) to leave (S)-2-amino-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethylpentan-1-one hydrochloride as an off-white solid which was used without further purification. TLC (Rf=0.0, EtOAc:heptane 2:1), analytical HPLC main peak, Rt=4.047 min., HPLC-MS 287.2 [M+H]+, 595.3 [2M+Na]+; δC (125 MHz, CD3OH) 29.66 (C(CH3)3), 30.45 (C(CH3)3), 44.51/49.24 (NCH2CHOCH3 and CH2C(CH3)3), 50.03 (CHCH2C(CH3)3), 57.85 (OCH3), 70.64 (CHCHOH), 74.83 (CHCHOH), 75.56 (CH2CHOH), 78.13 and 79.11 (CHCHOCH3), 169.80/169.98 (NC═O).

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue azeotroped with toluene (1×50 mL

Sources & evidence

ORD record
ord-dcae17170f4045d49485121398015d0b
Source dataset
uspto-grants-2010_09
Patent number
US07803803B2

Reaction notes

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