Chloroacetic Acid → HCID 131724484, compound

HRID 1883300Notes

Reaction equation

HRID 1883300 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:33]([OH:35])=[O:34])[CH2:14][CH2:15][CH2:16][CH2:17][NH:18]S(C1C(C)=C(C)C(OC)=CC=1C)(=O)=O)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:36][C:37]([NH:48][CH2:49][CH:50]([OH:66])[CH2:51][O:52][C:53]1[C:58]2[C:59]3[C:64]([NH:65][C:57]=2[CH:56]=[CH:55][CH:54]=1)=[CH:63][CH:62]=[CH:61][CH:60]=3)([C:39]1[CH:44]=[CH:43][C:42]([N:45]=[N+:46]=[N-:47])=[CH:41][CH:40]=1)[CH3:38].C1(OC)C=CC=CC=1.ClCC(O)=O.C(OCC)(=O)C>C(Cl)Cl>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:33]([OH:35])=[O:34])[CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:38][C:37]([NH:48][CH2:49][CH:50]([OH:66])[CH2:51][O:52][C:53]1[C:58]2[C:59]3[C:64]([NH:65][C:57]=2[CH:56]=[CH:55][CH:54]=1)=[CH:63][CH:62]=[CH:61][CH:60]=3)([C:39]1[CH:44]=[CH:43][C:42]([N:45]=[N+:46]=[N-:47])=[CH:41][CH:40]=1)[CH3:36]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 7519AnisoleHCID 8857Ethyl AcetateHCID 131724485HCID 131724485, compound

Product 1

HCID 131724484HCID 131724484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of MEt-IDA-(Phe-Lys(Mtr)-PABC-MMC)2 30 (134.6 mg, 0.0590 mmol) in methylene chloride (3 mL) at rt was treated with anisole (1.28 mL, 200 equiv) and 1 M chloroacetic acid in methylene chloride (1.18 mL, 20 equiv). After 3.5 h ethyl acetate (30 mL) was added. The resulting purple solid was collected by filtration, washed with ethyl acetate and air-dried (97.8 mg, 82%). The product appeared to decompose in solution to one product by HPLC. 1H-NMR (CDCl3/CH3OD) δ 1.33 (m, 4H), 1.63 (s and M, 12H), 1.77 (m, 2H), 2.52 (m, 2H), 2.82 (m, 6H), 3.03 (m, 2H), 3.10 (s and brs, 10H), 3.27 (m, 2H), 3.53 (ABq, 2H), 3.96 (brs, 4H), 4.11 (m, 2H), 4.35 (d and m, 3H), 4.53 (m, 2H), 4.78 (ABq, 2H), 4.94 (m, 4H), 6.62 (s, 2H), 7.10 (m, 10H), 7.19 (d, 4H), 7.41 (d, 4H). MS (FAB) 1738.3 (M+Na)+, 1776.4 (M+K)+.

Workup

  1. filtrationThe resulting purple solid was collected by filtration
  2. washwashed with ethyl acetate
  3. customair-dried (97.8 mg, 82%)

Sources & evidence

ORD record
ord-eb295e399f934dd98d4db6dcbed61461
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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