Ammonium Acetate → HCID 70285547, compound

HRID 362140Notes

Reaction equation

HRID 362140 reaction equation
[C:1]([CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:23]([NH:25][C@H:26]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:51]([NH:53][C@H:54]([B:59]1[O:63][C@@H]2C[C@@H]3C[C@H]([C@]2(C)[O:60]1)C3(C)C)[CH2:55][CH2:56][CH2:57][CH3:58])=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=[O:44])[C:39]([CH3:42])([CH3:41])[CH3:40])=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:24])[CH2:18][CH2:19][C:20](=[O:22])[OH:21])=[O:15])[CH2:10][C:11](=[O:13])[OH:12])=[O:7])([OH:3])=[O:2].C([O-])(=O)C.[NH4+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O>[C:1]([CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:23]([NH:25][C@H:26]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:51]([NH:53][C@H:54]([B:59]([OH:60])[OH:63])[CH2:55][CH2:56][CH2:57][CH3:58])=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=[O:44])[C:39]([CH3:42])([CH3:41])[CH3:40])=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:24])[CH2:18][CH2:19][C:20](=[O:21])[OH:22])=[O:15])[CH2:10][C:11](=[O:12])[OH:13])=[O:7])([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodate2×HCID 86753713HCID 86753713, compound

Product 1

HCID 70285547HCID 70285547, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

0.2 g (0.2 mmol) of N2-[N-[N-[N-[N-(carboxypropionyl)-L-α-aspartyl]-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl -L-valyl]-N1-[1(R)-(3a(S),4(S),5,6(S),7,7a(R)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl)pentyl]-L-leucinamide was dissolved in 12 ml of acetone and 12 ml of 0.1M ammonium acetate in water were added. 0.21 g (1 mmol) of sodium periodate was added and the resulting mixture was stirred at room temperature for 22 hours. 7 ml of water were then added together with a small amount of sodium periodate. The resultingsolution was stirred for a further 5 hours. The acetone was removed under avacuum and the aqueous residue was acidified with 2N hydrochloric acid and then extracted with ethyl acetate. Saturated aqueous sodium chloride was added to the aqueous layer which was then extracted with ethyl acetate. The organic extracts were combined, dried over sodium sulphate and evaporated. The residue was trituated with diethyl ether, filtered off anddried to give 167 mg of 1(R)-[[N-[N-[N-[N-[N-(3-carboxypropionyl)-L-α-aspartyl]-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]amino]pentylboronic acid as a white solid; MS: m/e 845.4 [M+H-H2O]+.

Workup

  1. stirringThe resultingsolution was stirred for a further 5 hours
  2. customThe acetone was removed under avacuum
  3. extractionextracted with ethyl acetate
  4. additionSaturated aqueous sodium chloride was added to the aqueous layer which
  5. extractionwas then extracted with ethyl acetate
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. filtrationfiltered off anddried

Sources & evidence

ORD record
ord-a47d42dd7928448aa4aee1134a4c241e
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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