Acetonitrile → HCID 57684686, compound

HRID 425045Notes

Reaction equation

HRID 425045 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([C@H:17]2[C@H:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:21]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:19]([CH2:47][O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[O:18]2)=[CH:13][C:3]=1[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.CC#N.[CH:59]1([NH2:62])[CH2:61][CH2:60]1.[BH3-]C#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([C@H:17]2[C@H:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:21]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C@@H:19]([CH2:47][O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[O:18]2)=[CH:13][C:3]=1[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:62][CH:59]2[CH2:61][CH2:60]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 57684689HCID 57684689, compound

Product 1

HCID 57684686HCID 57684686, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzaldehyde (intermediate AP) (40 mg) in CH2Cl2:CH3CN (v/v=1:1) (1.0 mL) was cooled to 0° C., followed by addition of cyclopropylamine (15 mg) and acetic acid (1 mg). After 30 min, NaBH3CN (17 mg) was added. The reaction was monitored by LC-MS. After the starting material was consumed, ethyl acetate (20 mL) and water (5 mL) were added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic extracts were combined and washed with brine. Removal of ethyl acetate under reduced pressure and purification of the crude product by preparative TLC gave intermediate AQ (30 mg). MS ESI (m/z): 794 (M+H)+.

Workup

  1. customAfter the starting material was consumed
  2. additionethyl acetate (20 mL) and water (5 mL) were added
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washwashed with brine
  8. customRemoval of ethyl acetate
  9. customunder reduced pressure and purification of the crude product by preparative TLC
  10. customgave intermediate AQ (30 mg)

Sources & evidence

ORD record
ord-762aa1a28e1d42df8957667b41166cc0
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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