Acetic Acid → HCID 89590858, compound

HRID 522419Notes

Reaction equation

HRID 522419 reaction equation
[C:1]([C@H:5]1[C:33](=[O:34])[N:32]2[CH2:35][C@@H:29]([CH2:30][C@H:31]2[C:36]([O:38][CH3:39])=[O:37])[O:28][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([CH:26]=O)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:40][C@H:9]2[O:8][C:7](=[O:41])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([C@H:5]1[C:33](=[O:34])[N:32]2[CH2:35][C@@H:29]([CH2:30][C@H:31]2[C:36]([O:38][CH3:39])=[O:37])[O:28][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([CH2:26][N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:40][C@H:9]2[O:8][C:7](=[O:41])[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 89590877HCID 89590877, compound

Product 1

HCID 89590858HCID 89590858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step 2 (34 mg, 0.060 mmol) in CH2Cl2 (3 ml) was added morpholine (0.016 ml, 0.180 mmol) and acetic acid (10.32 μl, 0.180 mmol) followed by sodium triacetoxyborohydride (38.2 mg, 0.180 mmol). The reaction was complete in 30 minutes at which stage it was quenched with water and extracted with dichloromethane. Purification by PTLC (40% EtOAc/hexane) provided the desired compound.

Workup

  1. customwas quenched with water
  2. extractionextracted with dichloromethane
  3. customPurification by PTLC (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-2ffe159cc5814eefaea42b22bf7210d2
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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