Acetic Acid → (R)-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-2-[4-(1-oxo-1lambda4-thiomorpho-lin-4-yl)-piperidin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 1864621Notes

Reaction equation

HRID 1864621 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:28][C:29]3[CH:38]=[C:37]([CH3:39])[C:32]4[NH:33][C:34](=[O:36])[O:35][C:31]=4[CH:30]=3)[C:19](=[O:27])[N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[NH:3]1.[NH:44]1[CH2:49][CH2:48][S:47](=[O:50])[CH2:46][CH2:45]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@H:18]([CH2:28][C:29]3[CH:38]=[C:37]([CH3:39])[C:32]4[NH:33][C:34](=[O:36])[O:35][C:31]=4[CH:30]=3)[C:19](=[O:27])[N:20]3[CH2:21][CH2:22][CH:23]([N:44]4[CH2:49][CH2:48][S:47](=[O:50])[CH2:46][CH2:45]4)[CH2:24][CH2:25]3)=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 12600299Thiomorpholine 1-oxideHCID 69058954(R)-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 16049318(R)-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-2-[4-(1-oxo-1lambda4-thiomorpho-lin-4-yl)-piperidin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 80 mg (0.14 mmol) (R)-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-2-(4-oxo-piperidin-1-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate and 32 mg (0.27 mmol) thiomorpholin-1-oxide in 5 mL DCM was stirred overnight at RT. After the solution had been cooled to 0° C., 15 μL (0.27 mmol) of AcOH and 50 mg (0.33 mmol) of sodium triacetoxyborohydride were added and the reaction mixture was stirred for 4 h at this temperature. It was evaporated down i.vac., the residue was taken up in 1 mL MeOH, filtered to remove any insoluble constituents and the crude product was purified by HPLC. The fractions containing the product were combined and lyophilised.

Workup

  1. customIt was evaporated down i.vac
  2. filtrationfiltered
  3. customto remove any insoluble constituents
  4. customthe crude product was purified by HPLC
  5. additionThe fractions containing the product

Sources & evidence

ORD record
ord-81ab490796cd4fff93924ae5293cf30f
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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