Hydrochloric Acid → (3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine

HRID 82439

反応式

HRID 82439 の反応式
[NH2:1][C@H](C(O)=O)C.C([O-])=O.[Na+].OP([O-])([O-])=O.[Na+].[Na+].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.[CH2:78]([O:85][C@@H:86]1[C:91](=O)[CH2:90][CH2:89][O:88][CH2:87]1)[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH2:78]([O:85][C@@H:86]1[C@@H:91]([NH2:1])[CH2:90][CH2:89][O:88][CH2:87]1)[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1

参加物

11

反応物 8

HCID 313Hydrochloric AcidHCID 1051Pyridoxal 5'-phosphateHCID 5950L-AlanineHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 439153NadhHCID 2723810Sodium FormateHCID 60209906(3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one

生成物 1

HCID 60209907(3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of L-Alanine (200 g, 2.24 mol), sodium formate (76.0 g, 1.12 mmol), and sodium phosphate dibasic (28.7 g, 202 mmol) in 2.25 L of water adjusted to pH 7.5 was added NAD (2.2 g, 3.21 mmol), pyridoxal-5-phosphate (2.2 g, 8.90 mmol), LDH (0.45 g, 0.22 mol), FDH (4.5 g, 0.20 mol), and TA P1 G5 (4.5 g, 0.22 mol). After all the components were completely dissolved, (3S)-3-(benzyloxy)tetrahydro-4H-pyran-4-one (45 g, 0.22 mol) was added and the pH was adjusted to pH 7.25 with 6 N HCl and aged at 30° C. After 15 h, potassium carbonate (700 g, 5.06 mol) was added slowly, followed by ethyl acetate (2.2 L). The mixture was filtered through a bed of Solka Floc and the cake was washed with ethyl acetate (250 mL). The combined filtrates were separated and the aqueous layer was extracted a second time with ethyl acetate (2 L). The combined organic extracts were concentrated in vacuo to provide crude (3R,4S)-3-(benzyloxy)tetrahydro-2H-pyran-4-amine.

後処理

  1. dissolutionAfter all the components were completely dissolved
  2. customaged at 30° C
  3. filtrationThe mixture was filtered through a bed of Solka Floc
  4. washthe cake was washed with ethyl acetate (250 mL)
  5. customThe combined filtrates were separated
  6. extractionthe aqueous layer was extracted a second time with ethyl acetate (2 L)
  7. concentrationThe combined organic extracts were concentrated in vacuo

出典と根拠

ORDレコード
ord-07225e619eb640e285f6fccc978913dc
出典データセット
uspto-grants-2014_09
特許番号
US08846702B2

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