Sarcosine → (n-Methyl)glycyl biotin

HRID 1901413Notes

Reaction equation

HRID 1901413 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][CH2:10][C:11]([OH:13])=O.O[N:15]1[C:36](=[O:37])[NH:35][C@H:34]2[C@@H:16]1[CH2:17][S:18][C@H:19]2[CH2:20][CH2:21][CH2:22][CH:23](N1C(=O)CCC1=O)[C:24](=[O:26])[OH:25]>CN(C=O)C>[CH3:8][NH:9][CH2:10][C:11]([CH:23]([CH2:22][CH2:21][CH2:20][C@H:19]1[C@@H:34]2[C@@H:16]([NH:15][C:36]([NH:35]2)=[O:37])[CH2:17][S:18]1)[C:24](=[O:25])[OH:26])=[O:13]

Participants

5

Reactant 3

HCID 1088SarcosineHCID 8471TriethylamineHCID 129676281N-Hydroxysuccinimido-d-biotin

Product 1

HCID 53735751(n-Methyl)glycyl biotinYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

DMF (8.0 ml) and triethylamine (0.61 ml, 4.35 mmol) were added to solids N-methyl glycine (182 mg, 2.05 mmol) and N-hydroxy-succinimidyl biotin (500 mg, 1.46 mmol). The mixture was heated for 1 hour in an oil bath at 85° C. during which time the solids dissolved producing a clear and colorless solution. The solvents were then evaporated. The yellow oil residue was acidified with glacial acetic acid, evaporated and chromatographed on a 27 mm column packed with 50 g silica, eluting with 30% MeOH/EtOAc 1% HOAc to give the product as a white solid (383 mg) in 66% yield.

Workup

  1. dissolutiondissolved
  2. customproducing a clear and colorless solution
  3. customThe solvents were then evaporated
  4. customevaporated
  5. customchromatographed on a 27 mm column
  6. washeluting with 30% MeOH/EtOAc 1% HOAc

Sources & evidence

ORD record
ord-cd1d3c2e1f8d4411874b36c8df98d378
Source dataset
uspto-grants-1996_11
Patent number
US05578287

Reaction notes

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