Acetic Acid → HCID 178461770, compound

HRID 1486195Notes

Reaction equation

HRID 1486195 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([NH:14][C@H:15]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:18]=3[O:17][B:16]2[OH:28])=[O:13])[CH2:7][CH2:6]1.C(O)(=O)C.O=[CH:34][C@@H:35]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH3:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:40]([O:39][C:38]([NH:37][C@@H:35]([CH3:36])[CH2:34][NH:1][CH2:2][CH2:3][NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([NH:14][C@H:15]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:18]=3[O:17][B:16]2[OH:28])=[O:13])[CH2:7][CH2:6]1)=[O:44])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamateHCID 178511351HCID 178511351, compound

Product 1

HCID 178461770HCID 178461770, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-3-(2-(trans-4-(2-aminoethylamino)cyclohexyl)acetamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid from Example 15 (92 mg) in MeOH (2 mL) was added TEA (70 μL), acetic acid (30 μL), (S)-tert-butyl 1-oxopropan-2-ylcarbamate (86 mg) and sodium triacetoxyborohydride (212 mg). The reaction mixture was stirred overnight at RT. Solvent was removed and the product was carried on to next step without further purification.

Workup

  1. customSolvent was removed
  2. customthe product was carried on to next step without further purification

Sources & evidence

ORD record
ord-d052219273d145f18ff247c9e41d8d57
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

Loading…