Formaldehyde → HCID 56638510, compound

HRID 375766Notes

Reaction equation

HRID 375766 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:22]2[CH2:21][S:20][CH2:19][C@@H:18]([C:23]([O:25][CH3:26])=[O:24])[NH:17][C:16](=[O:27])[C@@H:15]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:14][O:13][C:12](=[O:36])[C:11]=2[CH:10]=[C:9]([N:37]2[C:45](=O)C3C(=CC=CC=3)[C:38]2=O)[CH:8]=1)(C)(C)C.[BH4-].[Na+].S(=O)(=O)(O)O.C=O>O1CCCC1.C(OCC)(=O)C>[OH:6][C:7]1[C:22]2[CH2:21][S:20][CH2:19][C@@H:18]([C:23]([O:25][CH3:26])=[O:24])[NH:17][C:16](=[O:27])[C@@H:15]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:14][O:13][C:12](=[O:36])[C:11]=2[CH:10]=[C:9]([N:37]([CH3:45])[CH3:38])[CH:8]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 53751378HCID 53751378, compound

Product 1

HCID 56638510HCID 56638510, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 47 mg of the product of Example 159 and 27 mg of sodium borohydride in 5 ml of tetrahydrofuran was added within 10 minutes to a mixture of 0.08 ml of 6N sulfuric acid and 0.05 ml of 40% aqueous formaldehyde in 2 ml of tetrahydrofuran at 0° C. Stirring was continued for 4 hours at 0° C. The mixture was diluted with ethyl acetate, and then washed with 10% sodium carbonate solution and with brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate/diethylether to give 25 mg of tert-butyl (4R, 7S)-1,3,4,5,6,7,8,10-octahydro-14-hydroxy-4-methoxycarbonyl-12-dimethylamino-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid.

Workup

  1. washwashed with 10% sodium carbonate solution and with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was crystallized from ethyl acetate/diethylether

Sources & evidence

ORD record
ord-a09d6d55c13c4963bc5be20420fd5cb0
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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