Boc-Asp(O-cHex) Man(4-MBzl) → Asp(O-cHex) Man(4-MBzl)

HRID 263498

Reaction equation

HRID 263498 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4](=[O:12])[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH:23][CH:24]1[O:40][C@H:39]([CH2:41][OH:42])[C@@H:29]([O:30][CH2:31][C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)[C@H:27]([OH:28])[C@@H:25]1[OH:26]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4](=[O:12])[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH:23][CH:24]1[O:40][C@H:39]([CH2:41][OH:42])[C@@H:29]([O:30][CH2:31][C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)[C@H:27]([OH:28])[C@@H:25]1[OH:26]

Participants

3

Reactant 1

HCID 131720065Boc-Asp(O-cHex) Man(4-MBzl)

Product 1

HCID 131720066Asp(O-cHex) Man(4-MBzl)Yield 107.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Boc-Asp(O-cHex)-Man(4-MBzl) (52 g) was treated with 50% TFA/methylene chloride (400 mL) for 45 min at room temperature. The solvent was evaporated and chased several times with methylene chloride to eliminate traces of TFA. The product precipitated as its TFA salt upon addition of ether. The solid was collected and air dried to yield a white solid (46.7 g, 88%).

Workup

  1. customThe solvent was evaporated
  2. customThe product precipitated as its TFA salt upon addition of ether
  3. customThe solid was collected
  4. customair dried

Sources & evidence

ORD record
ord-ce3cf141d3b541f7b31680b4023b0da8
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Linked notes

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